UPCOMING EVENTS (76)

events happening in the next 30 days

USNA Commissioning Week
Navy-Marine Corps Memorial Stadium

  May 17th - May 24th, 2019 The United States Naval Academy prepares for a week of tradition, ceremony, and celebration for its gradua ...

Architrex Tours
Watermark Tours, Charters, Cruises

The historic district of Annapolis is a museum without walls, a treasure trove of architecture and preservation. Celebrate and learn about t ...

Chow for a Cause
Navy-Marine Corps Memorial Stadium

**THIS IS A RAIN OR SHINE EVENT** SPONSOR EVENT | VOLUNTEER | VENDORS   When Charity Meets Food Trucks, You Get The Best of it All What a ...

N.E.W. athens Performing the Music of R.E.M.
Rams Head On Stage

N.E.W. Athens is a band dedicated to performing the music of R.E.M. including the classics, the big hits, and the deep cuts. They’ve pe ...

Rodney Crowell
Rams Head On Stage

Classics can become cliches. And cliches, like whiskey, nostalgia, and orthodoxy, will deaden the mind. We can’t learn from what we k ...

Preacher Lawson
Rams Head On Stage

I was born In Portland, Oregon, but raised most of my adolescence in Memphis, TN. I moved 20 times before age 10, but if you asked me what c ...

Preacher Lawson
Rams Head On Stage

I was born In Portland, Oregon, but raised most of my adolescence in Memphis, TN. I moved 20 times before age 10, but if you asked me what c ...

The Temptations at Maryland Hall for the Creative Arts
Maryland Hall

For more than fifty years, The Temptations have prospered, propelling popular music with a series of smash hits and sold-out performances th ...

Acoustic Brunch with Music by Gareth Asher
Annapolis Waterfront Hotel Dock

An Intimate, Acoustic Show with Memorial Day favorite, Gareth Asher aboard the Schooner Woodwind for a concert on a beautiful sailing bo ...

Memorial Day Parade
Downtown Historic Annapolis

When: May 27th, 2019Where: Parade kicks off at Amos Garrett Boulevard and West St., Annapolis The parade will follow the traditional route w ...

Bay Lighthouses Cruise
Watermark Tours, Charters, Cruises

Pass under the twin spans of the Bay Bridges and by Sandy Point Shoal, Baltimore Harbor, and Thomas Point lighthouses. A historically attir ...

The English Beat
Rams Head On Stage

One of the most popular and influential ska groups, The English Beat, rushed on to the music scene in 1979. With Dave Wakeling on vocals and ...

Dinner Under the Stars
Inner West Street Association

Dinner Under the Stars is a place for families and friends to come together and for romantic evenings under the stars.  This summer spend W ...

Tommy Tutone
Rams Head On Stage

Tommy Tutone are classic '80s rockers led by vocalist and guitarist Tommy Heath, best known for the worldwide smash "867-5309/Jenny". The g ...

Bay Lighthouses Cruise
Watermark Tours, Charters, Cruises

Pass under the twin spans of the Bay Bridges and by Sandy Point Shoal, Baltimore Harbor, and Thomas Point lighthouses. A historically attir ...

Annapolis Greek Festival
Sts. Constantine & Helen Greek Orthodox Church

The Greeks call it Kefi – when the music is playing and the joys of life consume you making you want to jump, dance and yell OPA! The ...

The Docksiders (Dance Floor!)
Rams Head On Stage

Imagine that it’s 1981 and you’re cruising the Atlantic shores of the Hamptons with your friends. Bikinis are fluorescent, polo co ...

Annapolis Greek Festival
Sts. Constantine & Helen Greek Orthodox Church

The Greeks call it Kefi – when the music is playing and the joys of life consume you making you want to jump, dance and yell OPA! The ...

Agatha Christie's Towards Zero
Colonial Players of Annapolis

When a house party gathers at Gull's Point, the seaside home of Lady Tressilian, Neville Strange finds himself caught between his old wife A ...

Cowboy Mouth
Rams Head On Stage

For over two decades, Cowboy Mouth has dished up its unique style of rock & roll gumbo, mixing a rowdy spirit reflective of the band's h ...

Annapolis Greek Festival
Sts. Constantine & Helen Greek Orthodox Church

The Greeks call it Kefi – when the music is playing and the joys of life consume you making you want to jump, dance and yell OPA! The ...

Bay Bridge Paddle
Sandy Point State Park

Sandy Point State Park, Annapolis, MDSaturday, June 1st, 2019Water enthusiasts of all ages and expertise are invited to join us at the Bay B ...

Chris Duarte & Indigenous
Rams Head On Stage

Indigenous Mato Nanji, longtime front man of Native American band Indigenous, makes an effort to improve his craft with each record. His pla ...

Hannah Wicklund
Rams Head On Stage

Hannah Wicklund & The Steppin Stones are fronted by a 21-year-old powerhouse guitarist, vocalist and songwriter. The South Carolina-born ...

Secret Garden Tour
Hammond-Harwood House

The 2019 historic Hammond- Harwood House Secret Garden Tour features private gardens in the Historic District of Annapolis. The area betwe ...

Annapolis Greek Festival
Sts. Constantine & Helen Greek Orthodox Church

The Greeks call it Kefi – when the music is playing and the joys of life consume you making you want to jump, dance and yell OPA! The ...

Secret Garden Tour
Hammond-Harwood House

The 2019 historic Hammond- Harwood House Secret Garden Tour features private gardens in the Historic District of Annapolis. The area betwe ...

Agatha Christie's Towards Zero
Colonial Players of Annapolis

When a house party gathers at Gull's Point, the seaside home of Lady Tressilian, Neville Strange finds himself caught between his old wife A ...

Big Bucks Bingo
Chesapeake Bay Beach Club

NOW HOME OF THE $12,500 JACKPOT!Upstairs Doors:  9:00 amAdvanced Sales Pickup:  12:30 pmUpstairs Admission:  2:00 pmDownstairs Doors:  ...

Legal Action
Rod 'N' Reel Resort

Maryland's Premier Classic Rock band featuring band members: Dave - Rhythm Guitar / Vocals,Scott - Lead Guitar,Chris- Lead Vocals / Guitar, ...

Vanessa Collier
Rams Head On Stage

If you haven’t been fortunate enough to meet Vanessa Collier and witness one of her head-turning, fiery, and passionate performances, y ...

Melanie Fiona
Rams Head On Stage

Just like the powerful music itself, Melanie Fiona exudes a soulful charm, wit and a genuine story-telling ability that expresses both vulne ...

Yonder Mountain String Band
Rams Head On Stage

Yonder Mountain String Band’s first new album in two years, LOVE. AIN’T LOVE is undeniably the Colorado-based progressive bluegras ...

Dinner Under the Stars
Inner West Street Association

Dinner Under the Stars is a place for families and friends to come together and for romantic evenings under the stars.  This summer spend W ...

Agatha Christie's Towards Zero
Colonial Players of Annapolis

When a house party gathers at Gull's Point, the seaside home of Lady Tressilian, Neville Strange finds himself caught between his old wife A ...

Junior Brown
Rams Head On Stage

With his unique voice and songwriting, and even more unique double necked “Guit-Steel” guitar, there has absolutely never been any ...

Agatha Christie's Towards Zero
Colonial Players of Annapolis

When a house party gathers at Gull's Point, the seaside home of Lady Tressilian, Neville Strange finds himself caught between his old wife A ...

Mindi Abair & The Boneshakers
Rams Head On Stage

Two-time GRAMMY nominee Mindi Abair has made her mark as one of the most recognizable saxophonists in the US. You may know her as the saxoph ...

Opening Night: Free Friday Night Summer Concert Series
Annapolis Towne Centre

Join us for our Free Friday Night Summer Concert Series ~ 10 Year Anniversary Celebration! New Music Every Week (Lineup listed below.) Win ...

The Winstons
Rod 'N' Reel Resort

...

Architrex Tours
Watermark Tours, Charters, Cruises

The historic district of Annapolis is a museum without walls, a treasure trove of architecture and preservation. Celebrate and learn about t ...

14th Annual Bands in the Sand
Philip Merrill Environmental Center

2019 will be our 14th Annual Bands In The Sand party at and to benefit the Chesapeake Bay Foundation.   Cowboy Mouth was the musical head ...

Tal Wilkenfeld
Rams Head On Stage

Love Remains, Tal Wilkenfeld’s debut solo album for BMG, is a testament to the celebrated bassist’s unconventional journey. While ...

Agatha Christie's Towards Zero
Colonial Players of Annapolis

When a house party gathers at Gull's Point, the seaside home of Lady Tressilian, Neville Strange finds himself caught between his old wife A ...

Drag Brunch: Show Us Your Pride
Rams Head On Stage

Come kick off the beginning of Pride Month with another fabulous brunch at Rams Head on Stage. Annapolis Pride is happy to bring you the tal ...

June Wine In The Wind Sail
Annapolis Waterfront Hotel Dock

Join us for a two-hour sail around the Chesapeake Bay while sampling wonderful wines.  A representative from a winery will introduce you ...

Paul Gilbert of Mr. Big
Rams Head On Stage

From platinum album sales and number one chart success as a founding member of MR. BIG, to frightening the guitar community with new levels ...

Gaelic Storm
Rams Head On Stage

It’s hard to imagine a band just coming into their own after 20 years of success, but that’s exactly what makes a true anomaly. Th ...

Dinner Under the Stars
Inner West Street Association

Dinner Under the Stars is a place for families and friends to come together and for romantic evenings under the stars.  This summer spend W ...

Lorrie Morgan
Rams Head On Stage

Loretta Lynn Morgan was born to make music. Barely a teenager when she made her first, and everlasting, impression on country music fans, it ...

Agatha Christie's Towards Zero
Colonial Players of Annapolis

When a house party gathers at Gull's Point, the seaside home of Lady Tressilian, Neville Strange finds himself caught between his old wife A ...

The Slambovian Circus of Dreams
Rams Head On Stage

Formed in Sleepy Hollow, New York over a decade ago, The Slambovian Circus of Dreams (AKA The Grand Slambovians) pioneered the Alt-Folk/Amer ...

Agatha Christie's Towards Zero
Colonial Players of Annapolis

When a house party gathers at Gull's Point, the seaside home of Lady Tressilian, Neville Strange finds himself caught between his old wife A ...

Darrell Scott
Rams Head On Stage

Darrell Scott is a Grammy-nominated performer and recording artist, a highly demanded multi-instrumentalist (he plays 13 instruments!), and ...

James Brice House Hard Hat Tour
Historic Annapolis, Inc.

Step inside the scaffolding at the James Brice House and discover preservation in progress both inside and out of this architectural gem! Ta ...

10-Year Anniversary Event
Terrapin Adventures

Celebrate 10 Years of Adventure with a deal so good, it's almost too good to be true (but we promise it's true)! It’s our 10-Year Anniv ...

Intern John's Revival Tour
Rams Head On Stage

Born and raised in St. Paul, Minnesota, he became “Intern John” when he started interning at his local radio station fresh out of ...

School Of Rock: Tribute to Led Zeppelin & Tribute to Indie Rock **All Ages Matinee**
Rams Head On Stage

School of Rock teaches guitar, bass, piano, drums, and vocals. They take students from the lesson room to the stage, developing confidence a ...

Agatha Christie's Towards Zero
Colonial Players of Annapolis

When a house party gathers at Gull's Point, the seaside home of Lady Tressilian, Neville Strange finds himself caught between his old wife A ...

Anna Nalick
Rams Head On Stage

Anna Nalick is hitting the road in 2019 with her fourth studio album, At Now. At Now is Anna’s first self produced album and features 1 ...

Father's Day Brews In The Breeze Sail
Annapolis Waterfront Hotel Dock

Sail on a lunchtime cruise on the Chesapeake Bay.  Lunch will be served buffet style while sailing on the beautiful Bay! Tickets are $88 pe ...

Father's Day Brunch Sail
Annapolis Waterfront Hotel Dock

This wonderful three-hour brunch cruise includes one free Bloody Mary or Mimosa and delicious food.  Menu: Bacon, Ham, Caramelized Onion an ...

Southside Johnny & The Asbury Jukes
Rams Head On Stage

Emerging in the '70's from the same New Jersey Shore music scene as his legendary contemporary and friend Bruce Springsteen, Southside's fir ...

The Band of Heathens & Will Hoge
Rams Head On Stage

The Band of Heathens - Americana stalwarts The Band of Heathens recently went into their hometown studio in Austin, TX deciding to record t ...

Steve Earle & The Dukes
Rams Head On Stage

Steve Earle, a man who doesn’t mind telling a story, was talking about the first thing Guy Clark ever said to him. “It was 1974, ...

Dinner Under the Stars
Inner West Street Association

Dinner Under the Stars is a place for families and friends to come together and for romantic evenings under the stars.  This summer spend W ...

11th Annual Paca Girlfriends Party
William Paca House and Garden

Celebrate 11 years of Paca Girlfriends at the social event of the season!  Enjoy an evening of food, fine wine, friendship, flowers, and f ...

Amy Grant
Rams Head On Stage

Conventional wisdom has it that Amy Grant put Contemporary Christian Music on the map, becoming the first CCM artist to have a platinum reco ...

Amy Grant
Rams Head On Stage

Conventional wisdom has it that Amy Grant put Contemporary Christian Music on the map, becoming the first CCM artist to have a platinum reco ...

Agatha Christie's Towards Zero
Colonial Players of Annapolis

When a house party gathers at Gull's Point, the seaside home of Lady Tressilian, Neville Strange finds himself caught between his old wife A ...

JD Simo Band
Rams Head On Stage

Acid rock, traditional blues, folk, soul, free form jazz, and the never ceasing desire to improvise form this mind bending kaleidoscope of s ...

Agatha Christie's Towards Zero
Colonial Players of Annapolis

When a house party gathers at Gull's Point, the seaside home of Lady Tressilian, Neville Strange finds himself caught between his old wife A ...

The English Channel: A Tribute to the British Invasion Decade
Rams Head On Stage

The English Channel meticulously recreates each song to sound just like the original recording and just like you remember it. At their show, ...

Architrex Tours
Watermark Tours, Charters, Cruises

The historic district of Annapolis is a museum without walls, a treasure trove of architecture and preservation. Celebrate and learn about t ...

The SMITHEREENS w. Special Guest Vocalist Marshall Crenshaw
Rams Head On Stage

Known for writing and playing catchy 1960s-influenced power pop that inspired countless alternative rockers, The Smithereens gained populari ...

The SMITHEREENS w. Special Guest Vocalist Marshall Crenshaw
Rams Head On Stage

Known for writing and playing catchy 1960s-influenced power pop that inspired countless alternative rockers, The Smithereens gained populari ...

ONGOING EXHIBITS (40)

annapolis art and culture

Eric Smith: Pen to Paint
Elizabeth Myers Mitchell Gallery/St. John's College

Eric Smith, the former political cartoonist for the Capital Gazette, created humorous and thought-provoking caricatures and drawings for mo ...

Water Views
Jo Fleming Contemporary Art

Contemporary and Abstract Landscapes and 3 dimensional work The Artists Sigrid Trumpy - Watercolor and Oil Paintings Eric Roberge - Painted ...

Eric Smith: Pen to Paint
Elizabeth Myers Mitchell Gallery/St. John's College

Eric Smith, the former political cartoonist for the Capital Gazette, created humorous and thought-provoking caricatures and drawings for mo ...

Water Views
Jo Fleming Contemporary Art

Contemporary and Abstract Landscapes and 3 dimensional work The Artists Sigrid Trumpy - Watercolor and Oil Paintings Eric Roberge - Painted ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Eric Smith: Pen to Paint
Elizabeth Myers Mitchell Gallery/St. John's College

Eric Smith, the former political cartoonist for the Capital Gazette, created humorous and thought-provoking caricatures and drawings for mo ...

Water Views
Jo Fleming Contemporary Art

Contemporary and Abstract Landscapes and 3 dimensional work The Artists Sigrid Trumpy - Watercolor and Oil Paintings Eric Roberge - Painted ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Eric Smith: Pen to Paint
Elizabeth Myers Mitchell Gallery/St. John's College

Eric Smith, the former political cartoonist for the Capital Gazette, created humorous and thought-provoking caricatures and drawings for mo ...

Water Views
Jo Fleming Contemporary Art

Contemporary and Abstract Landscapes and 3 dimensional work The Artists Sigrid Trumpy - Watercolor and Oil Paintings Eric Roberge - Painted ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Eric Smith: Pen to Paint
Elizabeth Myers Mitchell Gallery/St. John's College

Eric Smith, the former political cartoonist for the Capital Gazette, created humorous and thought-provoking caricatures and drawings for mo ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Eric Smith: Pen to Paint
Elizabeth Myers Mitchell Gallery/St. John's College

Eric Smith, the former political cartoonist for the Capital Gazette, created humorous and thought-provoking caricatures and drawings for mo ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Eric Smith: Pen to Paint
Elizabeth Myers Mitchell Gallery/St. John's College

Eric Smith, the former political cartoonist for the Capital Gazette, created humorous and thought-provoking caricatures and drawings for mo ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Eric Smith: Pen to Paint
Elizabeth Myers Mitchell Gallery/St. John's College

Eric Smith, the former political cartoonist for the Capital Gazette, created humorous and thought-provoking caricatures and drawings for mo ...

Water Views
Jo Fleming Contemporary Art

Contemporary and Abstract Landscapes and 3 dimensional work The Artists Sigrid Trumpy - Watercolor and Oil Paintings Eric Roberge - Painted ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Eric Smith: Pen to Paint
Elizabeth Myers Mitchell Gallery/St. John's College

Eric Smith, the former political cartoonist for the Capital Gazette, created humorous and thought-provoking caricatures and drawings for mo ...

Water Views
Jo Fleming Contemporary Art

Contemporary and Abstract Landscapes and 3 dimensional work The Artists Sigrid Trumpy - Watercolor and Oil Paintings Eric Roberge - Painted ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Eric Smith: Pen to Paint
Elizabeth Myers Mitchell Gallery/St. John's College

Eric Smith, the former political cartoonist for the Capital Gazette, created humorous and thought-provoking caricatures and drawings for mo ...

Water Views
Jo Fleming Contemporary Art

Contemporary and Abstract Landscapes and 3 dimensional work The Artists Sigrid Trumpy - Watercolor and Oil Paintings Eric Roberge - Painted ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Eric Smith: Pen to Paint
Elizabeth Myers Mitchell Gallery/St. John's College

Eric Smith, the former political cartoonist for the Capital Gazette, created humorous and thought-provoking caricatures and drawings for mo ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Eric Smith: Pen to Paint
Elizabeth Myers Mitchell Gallery/St. John's College

Eric Smith, the former political cartoonist for the Capital Gazette, created humorous and thought-provoking caricatures and drawings for mo ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Eric Smith: Pen to Paint
Elizabeth Myers Mitchell Gallery/St. John's College

Eric Smith, the former political cartoonist for the Capital Gazette, created humorous and thought-provoking caricatures and drawings for mo ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

Image & Imagination: Anne Arundel County Juried Exhibition 2019
Elizabeth Myers Mitchell Gallery/St. John's College

Our Bi-Annual Juried Exhibition featuring the work of Anne Arundel County Artists selected by Juror LuLen Walker, Art curator at Georgetown ...

WEEKLY HAPPENINGS (77)

entertainment while you're here

Happy Hour at Rams Head Tavern
Rams Head Tavern

Happy Hour is every Monday through Friday from 3-7pm! ...

Karaoke Live!
Live! Center Stage

Take Center Stage and be the star of the show at Karaoke Live! Sing your favorite songs with a live band to back you up! Seating available o ...

Live Music with Sean Hetrick and $6 Burgers
Reynolds Tavern

Join us for a great Wednesday night of music and $6 burgers, inside the 1747 Pub at Reynolds Tavern.  Listen to live music by Sean Hetrick ...

Amber North
Rams Head Tavern

Join us every Wednesday night for live music with Amber North! No cover! ...

Happy Hour at Rams Head Roadhouse
Rams Head Roadhouse

Happy Hour is every Monday through Friday from 3-7pm! ...

Live Music at Rams Head Dockside
Rams Head Dockside

Join us every Wednesday, Friday, and Saturday evening for free live music! No cover!  ...

Happy Hour at Rams Head Dockside
Rams Head Dockside

Happy Hour is every Monday through Friday from 3-7pm! ...

Four Centuries Walking Tour at 1:30 PM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Four Centuries Walking Tour at 10:30 AM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Wednesday Night Sailboat Races

The passion of sailing is front and center during the Annapolis Yacht Club’s annual Wednesday Night Sailboat Races. Some 130 crews ra ...

Annapolis Harbor & US Naval Academy Cruise
Watermark Tours, Charters, Cruises

A must-do Annapolis activity! Step aboard Harbor Queen for a narrated cruise of historic Annapolis Harbor and the banks of the U.S. Naval Ac ...

Wednesday Night Races
Annapolis Sailing Cruises: Schooner Woodwind

Woodwind and Woodwind II will be match racing every Wednesday night that there is an Annapolis Yacht Club (AYC) Race. Both boats will sta ...

Daily Sailing on the Chesapeake Bay
Annapolis Sailing Cruises: Schooner Woodwind

Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. Sail times are 11:00-1:00, 1:30-3:30, 4:00-6: ...

Wednesday Night Races
Annapolis Sailing Cruises: Schooner Woodwind

Woodwind and Woodwind II will be match racing every Wednesday night that there is an Annapolis Yacht Club (AYC) Race. Both boats will sta ...

Wednesday Night Races
Annapolis Sailing Cruises: Schooner Woodwind

Woodwind and Woodwind II will be match racing every Wednesday night that there is an Annapolis Yacht Club (AYC) Race. Both boats will sta ...

Happy Hour at Rams Head Tavern
Rams Head Tavern

Happy Hour is every Monday through Friday from 3-7pm! ...

Music: Pete Best
Rams Head Tavern

Join us every Thursday night for live music with Pete Best No cover! ...

Live Music at Brian Boru!
Brain Boru

Live music Thursday, Friday and Saturday nights, year round! ...

1/2 Price Maison Nicolas Wines
Reynolds Tavern

Every Thursday Night enjoy 1/2 Price bottles of Maison Nicolas Wines with food purchase.  Pinot Grigio, Chardonnay, Sauvignon Blanc, Merlot ...

Happy Hour at Rams Head Roadhouse
Rams Head Roadhouse

Happy Hour is every Monday through Friday from 3-7pm! ...

Happy Hour at Rams Head Dockside
Rams Head Dockside

Happy Hour is every Monday through Friday from 3-7pm! ...

Four Centuries Walking Tour at 1:30 PM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Four Centuries Walking Tour at 10:30 AM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Annapolis Harbor & US Naval Academy Cruise
Watermark Tours, Charters, Cruises

A must-do Annapolis activity! Step aboard Harbor Queen for a narrated cruise of historic Annapolis Harbor and the banks of the U.S. Naval Ac ...

Daily Sailing on the Chesapeake Bay
Annapolis Sailing Cruises: Schooner Woodwind

Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. Sail times are 11:00-1:00, 1:30-3:30, 4:00-6: ...

Crazy for You
Annapolis Summer Garden Theatre, Inc.

A zany rich-boy-meets-hometown-girl romantic comedy, CRAZY FOR YOU® tells the story of young New York banker Bobby Child, who is sent to De ...

Thursday Acoustic Music Sunset Sail
Annapolis Sailing Cruises: Schooner Woodwind

Sit back and relax as Don Shapelle & Don Sennett entertain you while sailing on the Chesapeake Bay. The cruise departs from the Annap ...

Happy Hour at Rams Head Tavern
Rams Head Tavern

Happy Hour is every Monday through Friday from 3-7pm! ...

Art & Story Time
Chesapeake Children's Museum

We are eager to share the passion for great children's literature and creative visual expression with our youngest visitors. Children ages t ...

Live Music at Killarney House!
Killarney House

Live music Every Friday and Saturday night at Killarney House. go to our website for current artist listings and schedules. ...

Friday Night Live!
Live! Center Stage

Friday Night Live! Join us for a night of fun and live entertainment as we bring you the top requested music at Live! Center Stage! 1st Fr ...

Live Music at Brian Boru!
Brain Boru

Live music Thursday, Friday and Saturday nights, year round! ...

Happy Hour at Rams Head Roadhouse
Rams Head Roadhouse

Happy Hour is every Monday through Friday from 3-7pm! ...

Live Music at Rams Head Dockside
Rams Head Dockside

Join us every Wednesday, Friday, and Saturday evening for free live music! No cover!  ...

Happy Hour at Rams Head Dockside
Rams Head Dockside

Happy Hour is every Monday through Friday from 3-7pm! ...

Four Centuries Walking Tour at 1:30 PM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Four Centuries Walking Tour at 10:30 AM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Annapolis Harbor & US Naval Academy Cruise
Watermark Tours, Charters, Cruises

A must-do Annapolis activity! Step aboard Harbor Queen for a narrated cruise of historic Annapolis Harbor and the banks of the U.S. Naval Ac ...

Oliver! The Musical
Annapolis Shakespeare Company

This popular Broadway musical based on the classic Charles Dickens tale about an orphan turned pickpocket is filled with pathos and drama, w ...

Daily Sailing on the Chesapeake Bay
Annapolis Sailing Cruises: Schooner Woodwind

Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. Sail times are 11:00-1:00, 1:30-3:30, 4:00-6: ...

Crazy for You
Annapolis Summer Garden Theatre, Inc.

A zany rich-boy-meets-hometown-girl romantic comedy, CRAZY FOR YOU® tells the story of young New York banker Bobby Child, who is sent to De ...

Historic Ghost Walk
Watermark Tours, Charters, Cruises

Haunted ghost tour at night with period dressed guides. Led by candlelight through historic Annapolis. Learn the city's most chilling tales. ...

Live Music at Killarney House!
Killarney House

Live music Every Friday and Saturday night at Killarney House. go to our website for current artist listings and schedules. ...

Live Music at Brian Boru!
Brain Boru

Live music Thursday, Friday and Saturday nights, year round! ...

Live Music at Rams Head Dockside
Rams Head Dockside

Join us every Wednesday, Friday, and Saturday evening for free live music! No cover!  ...

Four Centuries Walking Tour at 1:30 PM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Four Centuries Walking Tour at 10:30 AM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Chesapeake Bay Bridges Cruise
Watermark Tours, Charters, Cruises

Marvel at the engineering feat as you cruise under the twin spans of the Bay Bridges that connect the eastern and western shores of Maryland ...

Scenic Severn River Cruise
Watermark Tours, Charters, Cruises

A spectacular 6-mile cruise on the beautiful scenic Severn River. View the historic Annapolis Harbor including the banks of the U.S. Naval A ...

Thomas Point Lighthouse Cruise
Watermark Tours, Charters, Cruises

One of the most recognized lighthouses in Maryland, view this National Historic Landmark while cruising the Chesapeake Bay. Beer, Wine, mixe ...

Oliver! The Musical
Annapolis Shakespeare Company

This popular Broadway musical based on the classic Charles Dickens tale about an orphan turned pickpocket is filled with pathos and drama, w ...

Daily Sailing on the Chesapeake Bay
Annapolis Sailing Cruises: Schooner Woodwind

Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. Sail times are 11:00-1:00, 1:30-3:30, 4:00-6: ...

Oliver! The Musical
Annapolis Shakespeare Company

This popular Broadway musical based on the classic Charles Dickens tale about an orphan turned pickpocket is filled with pathos and drama, w ...

Day on the Bay to St. Michaels
Watermark Tours, Charters, Cruises

Cruise across the Bay to spend over three hours at this quaint, historic village, enjoying fresh seafood, boutique shopping and historic sit ...

Crazy for You
Annapolis Summer Garden Theatre, Inc.

A zany rich-boy-meets-hometown-girl romantic comedy, CRAZY FOR YOU® tells the story of young New York banker Bobby Child, who is sent to De ...

Historic Ghost Walk
Watermark Tours, Charters, Cruises

Haunted ghost tour at night with period dressed guides. Led by candlelight through historic Annapolis. Learn the city's most chilling tales. ...

Music: Skribe
Rams Head Tavern

Join us every Sunday night for live music with Skribe! No cover! ...

$5 Burger Night at Rams Head Tavern
Rams Head Tavern

Serving up delicious burgers every Sunday night for just $5! ...

Award-winning Sunday Brunch at Killarney House
Killarney House

Join us every Sunday for our award-winning Sunday Brunch featuring breakfast favorites plus Irish specialties from our kitchen! 10-2pm Every ...

Live Music Sundays at Galway Bay
Galway Bay

Join us for live Irish music every Sunday from 4-8pm in the pub! ...

Smooth Sundays
Live! Center Stage

Smooth Sundays Ease into the week with martinis and Jazz Music on Sundays from 6:00PM - 9:00PM ...

Award Winning Sunday Brunch Buffet at Brian Boru
Brian Boru

Join us for brunch every Sunday! Voted Best Brunch by What's Up Magazine 2 years in a row! ...

$5 Burger Night at Rams Head Dockside
Rams Head Dockside

Serving up delcious burgers for just $5 every Sunday from 4-10pm! ...

$5 Burger Night at Rams Head Roadhouse
Rams Head Roadhouse

Serving up delicious burgers every Sunday night for just $5 from 4-10pm! ...

Bottomless Bloody Mary Bar at Rams Head Tavern
Rams Head Tavern

We provide the fixin's, you provide the mixin'! Enjoy $10 Finlandia Bottomless Bloody Mary Bar with the purchase of an entree. ...

Sunday Brunch at Rams Head Dockside
Rams Head Dockside

Join us for Brunch every Sunday from 10 AM to 2 PM! ...

Four Centuries Walking Tour at 1:30 PM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Four Centuries Walking Tour at 10:30 AM
Watermark Tours, Charters, Cruises

A colonial attired tour guide brings history to life as you visit key sites – including the Maryland State House and the U.S. Naval Aca ...

Chesapeake Bay Bridges Cruise
Watermark Tours, Charters, Cruises

Marvel at the engineering feat as you cruise under the twin spans of the Bay Bridges that connect the eastern and western shores of Maryland ...

Scenic Severn River Cruise
Watermark Tours, Charters, Cruises

A spectacular 6-mile cruise on the beautiful scenic Severn River. View the historic Annapolis Harbor including the banks of the U.S. Naval A ...

Thomas Point Lighthouse Cruise
Watermark Tours, Charters, Cruises

One of the most recognized lighthouses in Maryland, view this National Historic Landmark while cruising the Chesapeake Bay. Beer, Wine, mixe ...

Thomas Point Lighthouse Cruise
Watermark Tours, Charters, Cruises

One of the most recognized lighthouses in Maryland, view this National Historic Landmark while cruising the Chesapeake Bay. Beer, Wine, mixe ...

Free Outdoor Movie Screenings
Reynolds Tavern

First of all, who doesn’t love a Free Movie Screening? Add the fact that it is outside under the beautiful Annapolis sky, and you autom ...

Annapolis Harbor & US Naval Academy Cruise
Watermark Tours, Charters, Cruises

A must-do Annapolis activity! Step aboard Harbor Queen for a narrated cruise of historic Annapolis Harbor and the banks of the U.S. Naval Ac ...

Daily Sailing on the Chesapeake Bay
Annapolis Sailing Cruises: Schooner Woodwind

Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. Sail times are 11:00-1:00, 1:30-3:30, 4:00-6: ...

Oliver! The Musical
Annapolis Shakespeare Company

This popular Broadway musical based on the classic Charles Dickens tale about an orphan turned pickpocket is filled with pathos and drama, w ...

Crazy for You
Annapolis Summer Garden Theatre, Inc.

A zany rich-boy-meets-hometown-girl romantic comedy, CRAZY FOR YOU® tells the story of young New York banker Bobby Child, who is sent to De ...