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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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Events & Festivals

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

The Time Jumpers was established in Nashville in 1998 by an assemblage of high-dollar studio musicians. As word spread along Music Row that something special was happening at Station Inn bluegrass clu...


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...

A troupe of Chesapeake Bay Troubadours celebrating life here in the "Land of Pleasant Living" and along the shores of the Chesapeake... through song and story, and mirth... The Eastport Oy...

Live Music at Brian Boru!

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

Live Music at Killarney House!

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

Summer Farm Series - Vine Yard Bash

Head out to Great Frogs Winery for you Friday night entertainment. Food trucks: Tiffany's Cattering, Taqueria Cabrito, Mad Flava, Music: The Bones of JR Jones Movie: Classic Silent F...

The Dan Band

Dan Finnerty caught America's attention as the foul-mouthed wedding singer in the hit film OLD SCHOOL, performing his now-infamous foul-mouthed rendition of "Total Eclipse of the Heart", as ...



Like the Hawaiian Islands themselves, HAPA's Pan-Polynesian music is an amalgam of infuences ranging from ancient genealogical chants to the strummed ballads of Portuguese fisherman, Spanish cowboys, ...

Infinity Theater Presents: "The Emperor's New Clothes"

  • Date: June 21, 2014 to August 02, 2014
  • Times: Saturdays 6/21, 6/28, 7/12, 7/19, 7/26, 8/2 at 11AM, Saturdays 7/19, 7/26, 8/2 at 2PM
  • Location: Infinity Theatre Company
  • Cost: Adults: $12.00, Children: $10.00

The Emperor's New Clothes by Hans Christian Andersen, adapted by E. Gray Simons III.  Grab your royal attire and hear the latest announcement from the News of the Realm... The Emperor loves fashi...

Live Music at Brian Boru!

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

Live Music at Killarney House!

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

Mid-Atlantic Brewsic Festival & Fire Truck show

  • Date: July 26, 2014
  • Times: Starting: 11:00 AM
  • Location: Anne Arundel County Fairgrounds
  • Cost: $20 Adults, $10 Designated Driver Tickets, FREE kids under 12

What is BREWSIC?? | broo-zik | the act of drinking a brew while listening to fabulous music. And what's better than drinking a cold brew while listening to good music? Drinking a cold brew and listeni...

Tyrone Wells

Tyrone Wells got his start as a singer-songwriter and storyteller in Southern California coffee shops, building a ground swell of devoted followers that connected with his powerful voice, honest lyric...


Bottomless Bloody Mary Bar

  • Date: Started March 31, 2013 (Every Sunday)
  • Times: Every Sunday, 10 AM - 2 PM
  • Venue: 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.

Jazz Brunch

  • Date: Started March 31, 2013 (Every Sunday)
  • Times: Every Sunday 10 AM - 2 PM, Jazz 11 AM - 2 PM
  • Venue: Rams Head Tavern

Join us for Brunch every Sunday from 10 AM to 2 PM and enjoy Live Jazz from 11 AM to 2 PM

No Moon Paddle

Our themed base No Moon Paddle invites folks down for an evening of paddling followed by a social gathering afterwards at the Nature Park. We will start at 5:30 and paddle until the sun starts to set...

“Satisfaction: The International Rolling Stones Show" is the international touring tribute show to one of the world's greatest Rock & Roll bands. Satisfaction is now celebrating their 1...


Debbie Davies: Debbie Davies has brought a new sensibility to the blues. The former guitarist for Albert Collins & the Icebreakers, Fingers Taylor & the Ladyfinger Revue, and Maggie Mayall &a...

Live Music: Tim Metz

Enjoy live music from Tim Metz every Monday on our Patio from 6-9 PM. No Cover

Trivia Night at 1747 Pub at Reynolds Tavern

Think you and your friends are smart? Every Monday night come test our your ability to think on the fly and compete against other teams for prizes. Teams of 1-12 can participate; but leave your cell...


"Comedy in The Courtyard"

"Comedy in the Courtyard" returns as The Annapolis Shakespeare company presents Moliere's The Schemings of Scapin (Through July 27) and "The Imaginary Invalid" August 5 - October 7...

Annual Alumni Concert

Take the whole family to City Dock to experience the USNA's Annual Alumni Concert.

Free World Beer Club Membership

  • Date: Started April 02, 2013 (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-...

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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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