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Annapolis Events & Festivals

Looking for things to do in Annapolis? Like to have fun? Like to keep busy? Like to create memories with loved ones? If so, it's time to head to our way. No matter what the season, Annapolis and the Chesapeake Bay is alive with a host of events and celebrations designed for the young and the young at heart. Whether you are outside on the water or inside one of our historic homes, there's an energy in the air here that keeps you coming back for more.

So what are you waiting for? Bring your family, invite your friends, indulge your senses. Join us for taste bud tingling events, quirky traditions, music to soothe your soul, and memories to last a lifetime.

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07-07-2015

Events & Festivals

Comedy in the Courtyard "Servant of Two Masters"

The Annapolis Shakespeare Company returns for their 3rd Season of "Comedy in the Courtyard". This season presenting "Servant of Two Masters". Carlo Goldoni's 18th-century farce fol...

Free World Beer Club Membership

  • Date: Started November 18, 2014 (Every Tuesday)
  • Times: Every Tuesday, All Day
  • Venue: Rams Head Tavern

Join our World Beer Club for free on Tuesdays. As a member you will be sample 100 beer from around the world. Upon completion you will receive your name on our WBC plaque, an engraved pewter mug, a t-...

Happy Hour at the John Barry

Stop in the John Barry Restaurant Monday - Friday from 4-7 pm for weekly cocktail and food specials! We're located inside the O'Callaghan Hotel on West Street. $2.00 off domestic bottles, rails, and...

Live Music: Swampcandy

Enjoy live music from Swampcandy every Tuesday in the Tavern from 10 PM to 1 AM.

Mike Zito & Acoustic Nighthawks

Mike Zito Mike has been getting worldwide acclaim for his work as front man for The Wheel, a hand-picked band Zito formed in 2012 and which includes acclaimed New Orleans saxophonist (and successive ...

MSC's "Romeo & Juliet" at ASGT

Annapolis Summer Garden Theatre is excited to welcome the Maryland Shakespeare Company (MSC) back to our stage, where they will perform one of William Shakespeare's classic plays. For three nights onl...

Pub Quiz Night

Pub Quiz night. Registration starts at 7:30. Teams compete to answer rounds of trivia questions. Winning team wins prize and chooses a charity to make a donation to.

Pub Trivia Night

Pub Trivia in 3 rounds with prizes for the winners! 7-9pm Bring a team and have some fun!

Rock the Dock Live ~ Live Music 7 Days a Week on our Beach!

Entertainment is a specialty at the Chesapeake Beach Resort and Spa. The beautifully recreated Band Shell on the dock offers concerts almost every night of the summer. Guests enjoy a variety of live b...

Sunset Sails & Beer Tasting with Heavey Seas Brewery

Sunset Sails & Beer Tasting, aboard a 74-foot, classic wooden schooner, Woodwind. We feel that everyone should be able to enjoy great, craft beer while sailing on the Chesapeake Bay. And on every ...

TUESDAYS AT CITY DOCK WITH THE USNA BAND

Join the the Naval Academy Band as they present five Tuesday night concerts this summer at the Annapolis City Dock’s Susan B. Campbell Park. Tuesday, July 7 Crabtowne Stompers 7:30 p.m. This...

USNA Band's Crabtowne Stompers - Annapolis City Dock

The Naval Academy Band’s Crabtowne Stompers will be performing at Susan B. Campbell Park at the Annapolis City Dock on Tuesday, July 7 at 7:30 p.m. The United States Naval Academy Band, “...

William Paca House and Garden

  • Date: March 20, 2015 to December 31, 2015 (Recurring daily)
  • Times: Monday through Saturday, 10:00 a.m. to 5:00 p.m. and Sunday, noon to 5:00 p.m.
  • Venue: William Paca House and Garden
  • Cost: $10 General Admission, $5 for children under 17, Free for HA members and volunteers

The William Paca House and Garden is a National Historic Landmark, restored by Historic Annapolis to its colonial-era splendor. Take some time to experience the 18th century life of lawyer, and signer...

07-08-2015

Happy Hour at the John Barry

Stop in the John Barry Restaurant Monday - Friday from 4-7 pm for weekly cocktail and food specials! We're located inside the O'Callaghan Hotel on West Street. $2.00 off domestic bottles, rails, and...

"In the Vane of..." is a concept that mixes the familiarity of your favorite songs along with new tunes inspired by a featured legendary artist - all performed by local Annapolis musicians -...

Karaoke Live!

  • Date: Started November 12, 2014 (Every Wednesday)
  • Times: Starting: 8:00 PM
  • Venue: Rams Head Center Stage
  • Cost: $5 at the door

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 on a first come first serve basis.

Live Music: Dean Rosenthal

Join us every Wednesday 5 - 8 PM on the patio for live music from Dean Rosenthal.

MSC's "Romeo & Juliet" at ASGT

Annapolis Summer Garden Theatre is excited to welcome the Maryland Shakespeare Company (MSC) back to our stage, where they will perform one of William Shakespeare's classic plays. For three nights onl...

Rock the Dock Live ~ Live Music 7 Days a Week on our Beach!

Entertainment is a specialty at the Chesapeake Beach Resort and Spa. The beautifully recreated Band Shell on the dock offers concerts almost every night of the summer. Guests enjoy a variety of live b...

Trivia Night at Two Rivers Steak & Fish House

Join us every Wednesday night for Charm City Trivia. Have a chance to win shots and prizes such as a $15 Two Rivers gift card. Enjoy a half priced bottle of select wines every Wednesday!

Wednesday Night Race Series

Woodwind and Woodwind II will be match racing every Wednesday night that there is an Annapolis Yacht Club (AYC) Race. Both boats will start on the AYC starting line at 6:45pm, and then race out to a s...

Wednesday Night Sailboat Races

  • Date: April 22, 2015 to September 02, 2015 (Every Wednesday)
  • Times: From: 6:10 PM to 8:00 PM
  • Location: Annapolis Harbor

Grab your favorite dockside seat in America's Sailing Capital to watch some 150 crews compete in midweek races that involve sailing around several marks in the Bay before heading back to Spa Creek f...

William Paca House and Garden

  • Date: March 20, 2015 to December 31, 2015 (Recurring daily)
  • Times: Monday through Saturday, 10:00 a.m. to 5:00 p.m. and Sunday, noon to 5:00 p.m.
  • Venue: William Paca House and Garden
  • Cost: $10 General Admission, $5 for children under 17, Free for HA members and volunteers

The William Paca House and Garden is a National Historic Landmark, restored by Historic Annapolis to its colonial-era splendor. Take some time to experience the 18th century life of lawyer, and signer...

07-09-2015

ASGT presents "Catch Me If You Can"

The second show of our 2015 season is a musical comedy about chasing your dreams…and not getting caught! "Catch Me If You Can" is a high-flying criminal caper based on the hit DreamWo...

Happy Hour at the John Barry

Stop in the John Barry Restaurant Monday - Friday from 4-7 pm for weekly cocktail and food specials! We're located inside the O'Callaghan Hotel on West Street. $2.00 off domestic bottles, rails, and...

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Annapolis & Anne Arundel County Conference & Visitors Bureau

26 West Street, Annapolis, MD 21401

Phone: 410.280.0445   Fax: 410.263.9591
Toll-free from the U.S. 888.302.2852

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