EVENTS BY MONTH

  • January
    January
    January

    Get out of the chilly weather this January and enjoy the art and dining scenes in Annapolis.

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  • February
    February
    February

    Ranked one of America’s Most Romantic Towns by Travel+Leisure Magazine, Annapolis is a great place to spend time in February.

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  • March
    March
    March

    Winter is coming to an end, and March is a wonderful time to beat the crowds and get a taste of the unique character of Annapolis.

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  • April
    April
    April

    Spring has arrived! Get out on the water, dine outside, join a tour, or take part in the many events happening in April.

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  • May
    May
    May

    From Blue Angel Flight demonstrations to food-packed events, May in Annapolis is all about being outside.

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  • June
    June
    June

    As summer rolls in, come enjoy Annapolis’ art, dining, history, on the water activities, and the many festivals and events in June.

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  • July
    July
    July

    July's sunny weather encourages locals and visitors alike to enjoy the area’s outdoor activities, events, and festivals.

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  • August
    August
    August

    Visiting Annapolis in August means one thing: Get out on the water! Climb aboard a sailboat or rent a kayak/paddleboard and cool off in the breeze.

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  • September
    September
    September

    Fewer crowds and cooler weather in September makes for a perfect weekend getaway in Annapolis.

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  • October
    October
    October

    Fall is here and so are the area’s seasonal festivals: Hayrides, haunted tours, and family-friendly events.

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  • November
    November
    November

    Rated one of the best cities for the holidays by Travel+Leisure, Annapolis in November is a great way to kick start the season.

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  • December
    December
    December

    With the holiday season in full swing, Annapolis is the perfect destination to find a special gift for everyone on your list.

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CALENDAR OF EVENTS

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WEEKLY HAPPENINGS (87)

entertainment while you're here

  • Trivia Night
    venue: Reynolds Tavern

    Final Score Maryland Presents Trivia every Monday night in the 1747 Pub. House cash prizes for the Top Three Teams! Teams from 1-12 people. ...

  • Lunes Latino with Patrick Alban & Noche Latina
    venue: Rams Head on Stage

    Spice up your night and heat up the dance floor with live salsa music! Patrick Alban & Noche Latina play music from Cuba and Latin Ameri ...

  • Happy Hour at Rams Head Dockside
    venue: Rams Head Dockside

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

  • Happy Hour at Rams Head Roadhouse
    venue: Rams Head Roadhouse

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

  • Happy Hour at Rams Head Tavern
    venue: Rams Head Tavern

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

  • Trivia Night at 1747 Pub at Reynolds Tavern
    venue: 1747 Pub at Reynolds Tavern - 7 Church Circle

    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 ...

  • Four Centuries Walking Tour at 1:30pm
    venue: 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
    venue: 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 ...

  • Pub Quiz Night
    venue: Galway Bay

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

  • Free World Beer Club Membership
    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 recei ...

  • Kids Night at The Rod 'N' Reel Restaurant
    venue: Chesapeake Beach Resort & Spa

    Kid's Night at the Rod 'N' Reel Restaurant Every Tuesday from 5-8pm Enjoy kids' activities and kids eat FREE with the purchase of an adult e ...

  • Pub Trivia Night at Brian Boru
    venue: Brian Boru

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

  • Groove Live!
    venue: Rams Head Center Stage

    Groove Live! Every Tuesday is Groove Live! here at Center Stage. Bringing the best bands around the DMV known for that unique Go-Go sound. ...

  • Happy Hour at Rams Head Dockside
    venue: Rams Head Dockside

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

  • Happy Hour at Rams Head Roadhouse
    venue: Rams Head Roadhouse

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

  • Happy Hour at Rams Head Tavern
    venue: Rams Head Tavern

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

  • Four Centuries Walking Tour at 1:30pm
    venue: 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
    venue: 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 ...

  • Live Music at Rams Head Roadhouse
    venue: Rams Head Roadhouse

    Free live music every Tuesday at 7:30PM! ...

  • Sunset Sails & Beer Tasting with Port City Brewery
    venue: Schooner Woodwind

    Sunset Sails & Beer Tasting, aboard a 74-foot, classic wooden schooner, Woodwind. We feel that everyone should be able to enjoy great, c ...

  • Annapolis Shakespeare Company's 'COMEDY IN THE COURTYARD'
    venue: Reynolds Tavern

    20  weeks  of  ASC’s  annual   ‘COMEDY  IN  THE  COURTYARD’  at  REYNOLDS  TAVERN Life is short. The complete work ...

  • Karaoke Live!
    venue: Rams Head 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 ...

  • $5 Burger Night at Reynolds Tavern
    venue: Reynolds Tavern

    Our 1/2 pound blend of short rib, ground chuck, & hangar steak on brioche roll with lettuce and tomato, and hand cut fries -- only $5 ev ...

  • Happy Hour at Rams Head Dockside
    venue: Rams Head Dockside

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

  • Happy Hour at Rams Head Roadhouse
    venue: Rams Head Roadhouse

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

  • Happy Hour at Rams Head Tavern
    venue: Rams Head Tavern

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

  • Four Centuries Walking Tour at 1:30pm
    venue: 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
    venue: 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 ...

  • Music: Amber North
    venue: Rams Head Tavern

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

  • Wednesday Night Race Series on board Schooner Woodwind
    venue: 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 start ...

  • Dinner Under the Stars
    venue: Inner West Street Association

    The first block of West Street (from Church Circle to Calvert Street), located in the heart of the Arts District, will be closed to traffi ...

  • DInner Under The Stars
    venue: West Street between Church Circle and Calvert Street

    Dine Al Fresco on Wednesday evenings on West Street under a canopy of lights. Participating restaurants include: Rams Head Tavern, Luna Blu, ...

  • Gene Gregory at Blackwall Hitch
    venue: Blackwall Hitch

    Join us for a live performance from Gene Gregory on Wednesday, May 31st at 7pm! ...

  • Live Music at Brian Boru!
    venue: Brain Boru

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

  • Happy Hour at Rams Head Dockside
    venue: Rams Head Dockside

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

  • Happy Hour at Rams Head Roadhouse
    venue: Rams Head Roadhouse

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

  • Happy Hour at Rams Head Tavern
    venue: Rams Head Tavern

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

  • Four Centuries Walking Tour at 1:30pm
    venue: 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
    venue: 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 ...

  • Music: Pete Best
    venue: Rams Head Tavern

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

  • Sunset Sails & Acoustic Music
    venue: Schooner Woodwind

    Sit back and relax as different local musicians entertain you while sailing on the Chesapeake Bay. The Singer/Songwriter genre will be well ...

  • Sister Act
    venue: Annapolis Summer Garden Theatre, Inc.

    A feel-good musical comedy smash based on the hit 1992 film starring Whoopi Goldberg, Sister Act is a sparkling tribute to the universal pow ...

  • Eric Scott at Blackwall Hitch
    venue: Blackwall Hitch

    Join us for a live performance from Eric Scott on Thursday, June 1st at 7pm! ...

  • Live Music at Killarney House!
    venue: Killarney House

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

  • Art & Story Time
    venue: 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 ...

  • First Fridays 80's Invasion
    venue: Rams Head Center Stage

    It's a totally awesome, true '80s EXPERIENCE every show! Doors: 8pm Show: 9pm Don't forget to swipe your Live! Rewards® card at the front d ...

  • Live Music at Brian Boru!
    venue: Brain Boru

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

  • Friday Night Live!
    venue: Rams Head Center Stage

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

  • Happy Hour at Rams Head Dockside
    venue: Rams Head Dockside

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

  • Happy Hour at Rams Head Roadhouse
    venue: Rams Head Roadhouse

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

  • Happy Hour at Rams Head Tavern
    venue: Rams Head Tavern

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

  • Four Centuries Walking Tour at 1:30pm
    venue: 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
    venue: 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 ...

  • Music: Loose Ties
    venue: Rams Head Tavern

    Join us every Friday night for live music with Loose Ties! No cover! ...

  • William Shakespeare's Richard III
    venue: Annapolis Shakespeare Company

    *** Intimate *** Powerful *** Compelling *** Richard III depicts the Machiavellian rise to power and subsequent short reign of King Richard ...

  • Sister Act
    venue: Annapolis Summer Garden Theatre, Inc.

    A feel-good musical comedy smash based on the hit 1992 film starring Whoopi Goldberg, Sister Act is a sparkling tribute to the universal pow ...

  • Historic Ghost Walk
    venue: Watermark Tours, Charters, Cruises

    As the sun sets and darkness wraps the streets of historic, and many say, haunted Annapolis, a period dressed guide will lead you on a journ ...

  • Historic Ghost Walk
    venue: Watermark Tours, Charters, Cruises

    As the sun sets and darkness wraps the streets of historic, and many say, haunted Annapolis, a period dressed guide will lead you on a journ ...

  • Friday Night Live! 80s w/ Guys in Thin Ties
    venue: Live! Casino & Hotel

    Rock out to the 1980’s new wave soundtrack the fourth Friday of every month as we journey though the decade’s top 100 billboard hi ...

  • The Shatners at Blackwall Hitch
    venue: Blackwall Hitch

    Join us for a live performance from The Shatners on Friday, June 2nd at 9:30pm! ...

  • Live Music at Killarney House!
    venue: 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!
    venue: Brain Boru

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

  • Four Centuries Walking Tour at 1:30pm
    venue: 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
    venue: 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 ...

  • William Shakespeare's Richard III
    venue: Annapolis Shakespeare Company

    *** Intimate *** Powerful *** Compelling *** Richard III depicts the Machiavellian rise to power and subsequent short reign of King Richard ...

  • Sister Act
    venue: Annapolis Summer Garden Theatre, Inc.

    A feel-good musical comedy smash based on the hit 1992 film starring Whoopi Goldberg, Sister Act is a sparkling tribute to the universal pow ...

  • Historic Ghost Walk
    venue: Watermark Tours, Charters, Cruises

    As the sun sets and darkness wraps the streets of historic, and many say, haunted Annapolis, a period dressed guide will lead you on a journ ...

  • Historic Ghost Walk
    venue: Watermark Tours, Charters, Cruises

    As the sun sets and darkness wraps the streets of historic, and many say, haunted Annapolis, a period dressed guide will lead you on a journ ...

  • Sly 45 at Blackwall Hitch
    venue: Blackwall Hitch

    Join us for a live performance from Sly 45 on Saturday June 3rd at 9:30pm! ...

  • Bottomless Bloody Mary Bar
    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
    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 ...

  • Live Music Sundays at Galway Bay
    venue: Galway Bay

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

  • Award-winning Sunday Brunch
    venue: Killarney House

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

  • Award Winning Sunday Brunch Buffet
    venue: 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
    venue: Rams Head Dockside

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

  • $5 Burger Night at Rams Head Tavern
    venue: Rams Head Tavern

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

  • $5 Burger Night at Roadhouse
    venue: Rams Head Roadhouse

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

  • Sunday Brunch
    venue: Rams Head Dockside

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

  • Smooth Sundays
    venue: Rams Head Center Stage

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

  • Sunday Night Free Outdoor Movie Screenings
    venue: Reynolds Tavern

    Free Classic Movie Screenings every Sunday Night April 2 - October 29 in the Outdoor Courtyard / Beer Garden at Reynolds Tavern.  All scree ...

  • Four Centuries Walking Tour at 1:30pm
    venue: 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
    venue: 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 ...

  • Music: Skribe
    venue: Rams Head Tavern

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

  • William Shakespeare's Richard III
    venue: Annapolis Shakespeare Company

    *** Intimate *** Powerful *** Compelling *** Richard III depicts the Machiavellian rise to power and subsequent short reign of King Richard ...

  • Sister Act
    venue: Annapolis Summer Garden Theatre, Inc.

    A feel-good musical comedy smash based on the hit 1992 film starring Whoopi Goldberg, Sister Act is a sparkling tribute to the universal pow ...

  • Smooth Sunday w/ Slim Man
    venue: Live! Casino & Hotel

    Baltimore's own Slim Man is coming to Live! CenterStage for a free jazz show. ...

  • Sunday Jazz Brunch
    venue: Blackwall Hitch

    Join us for a brunch buffet and live jazz performance form Unified Jazz Ensemble on Sunday, June 4th at 10am! ...