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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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07-29-2015

Events & Festivals

'The Handmade Quarterly' Vol. III feat. Higher Hands, Bumpin Uglies, Pressing Strings and Skribe

  • Date: July 29, 2015
  • Times: Doors 6:30pm / Show 7:30pm
  • Venue: Rams Head on Stage
  • Cost: $20.00

THE HANDMADE QUARTERLY is a revolving local concert series presented by DJ Boy/ Annapolis Records. Volume III will take place on Wednesday, July 29th at 7:30pm and will be a celebration of new music r...

Eye of the Beholder Exhibition

The 4th biennial Eye of the Beholder exhibition features artwork created with found objects. This diverse and funky exhibition is family friendly and free! A public reception will take place on July 2...

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...

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.

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...

07-30-2015

Damon Fowler & Jason Ricci

Damon Fowler With his hybrid of roots rock, blues, and sacred steel, Florida native Damon Fowler started wowing audiences with his musical exploits as a teenager, building a reputation as one of the ...

Eye of the Beholder Exhibition

The 4th biennial Eye of the Beholder exhibition features artwork created with found objects. This diverse and funky exhibition is family friendly and free! A public reception will take place on July 2...

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 at Brian Boru!

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

Live Music: Pressing Strings

Enjoy live music from Pressing Strings every Thursday in the Tavern from 10 PM to 1 AM

Open Mic Night

Come join us at Two Rivers Steak & Fish House for a night of fun and chance to show off your talents! Whatever your talent may be, such as singing, comedy, poetry, or event playing a instrument, w...

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...

Tides & Tunes Summer Concert Series

Ten weeks of folk, classic rock, soul, psychedelic funk, country, Hawaiian swing, Island music, boogie-woogie, and swing - all on the beach!

Tides and Tunes Outdoor Concert Series

Ten weeks of folk, classic rock, soul, psychedelic funk, country, Hawaiian swing, Island music, boogie-woogie, and swing - all on the beach!

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...

07-31-2015

42nd Annual St. Mary's College Governor's Cup Yacht Race

More than 100 yachts compete in the oldest and longest overnight race on the Chesapeake Bay. The 70-mile Annapolis race to St. Mary's City at the mouth of the Potomac River includes two separate sta...

Annapolis Towne Centre Free Friday Concerts

Every Friday night, the area's best talent will take the stage on Towne Centre Boulevard to deliver a rockin' performance. Enjoy local music, including classic rock, jazz, 80's, blues, swing and Motow...

Art & Story Time

We are eager to share the passion for great children's literature and creative visual expression with our youngest visitors. Children ages two to five years old and their accompanying adults can share...

Eye of the Beholder Exhibition

The 4th biennial Eye of the Beholder exhibition features artwork created with found objects. This diverse and funky exhibition is family friendly and free! A public reception will take place on July 2...

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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