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 (67)

entertainment while you're here

  • 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 ...

  • 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 ...

  • Live Music with Sean Hetrick and $6 Burger
    venue: Reynolds Tavern

    Join us every for a great Wednesday Night all Spring and Summer long in the Beer Garden with Live Music with Sean Hetrick and our 1/2 pound ...

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

    Join us every Wednesday evening for free live music! No cover!  ...

  • Artists in the Park - Wednesday Naptown Showcase
    venue: Maryland Theatre for the Performing Arts

    Maryland Theatre is launching an Wednesday artist showcase series throughout the summer in partnership with Naptownmusic to celebrate and pr ...

  • ASGT presents "The Full Monty"
    venue: Annapolis Summer Garden Theatre, Inc.

    Based on the hit film of the same name, The Full Monty is a heartwarming, upbeat comedy that entertains and grabs your heart. A ten-time T ...

  • Celebrate Summer in the Rosé Terrace
    venue: Reynolds Tavern

    We are hosting a Rosé party every Wednesday Night!!  First of all, not only do we love to drink Rosé, but we know it is the perfect S ...

  • Artists in the Park: Sean Hetrick
    venue: Maryland Theatre for the Performing Arts

    We are so happy to work with Naptownmusic to showcase these fine artists at our Stage One venue. With live music, great food and good friend ...

  • Steve Glazer at Blackwall Hitch
    venue: Blackwall Hitch

    Join us on Wednesday, July 19th at 7pm for a live performance from Steve Glazer.  ...

  • 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! ...

  • Thursday Night Dixie Hotel Jazz
    venue: Whitmore Park

    The Dixie Hotel was once part of the business district of the Annapolis Clay Street Community where famous personalities entertained standin ...

  • Tides & Tunes: Free Summer Concert Series
    venue: Annapolis Maritime Museum

    On Thursday nights this summer, bring the family to the Annapolis Maritime Museum to enjoy live music by local bands against the scenic back ...

  • ASGT presents "The Full Monty"
    venue: Annapolis Summer Garden Theatre, Inc.

    Based on the hit film of the same name, The Full Monty is a heartwarming, upbeat comedy that entertains and grabs your heart. A ten-time T ...

  • Gene Gregory at Blackwall Hitch
    venue: Blackwall Hitch

    Join us for a live performance from Gene Gregory on Thursday, July 20th 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 ...

  • 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! ...

  • 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 ...

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

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

  • ASGT presents "The Full Monty"
    venue: Annapolis Summer Garden Theatre, Inc.

    Based on the hit film of the same name, The Full Monty is a heartwarming, upbeat comedy that entertains and grabs your heart. A ten-time T ...

  • Zimmerman Legacy Tour & Bandstand Concerts at NAAA
    venue: U.S. Naval Academy Visitors Center

    A special Friday walking tour, featuring information on the USNA Band and the association of Charles Zimmerman with the U.S. Naval Academy, ...

  • Higher Hands at Blackwall Hitch
    venue: Blackwall Hitch

    Join us for a live performance from Higher Hands on Friday, July 21st at 9:30pm! ...

  • Two Roads Brewing Beer Tasting
    venue: Mills Fine Wine and Spirits

    Try great craft beers by Two Roads Brewing from Connecticut, available in pool and boat friendly cans. Save 15% if you decide to purchase an ...

  • 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 ...

  • 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 ...

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

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

  • California Wine Tasting
    venue: Mills Fine Wine and Spirits

    You'll be California dreaming trying some of our favorite Chardonnay, Pinot Noir and Zinfandel from the West Coast! Join us in samping and s ...

  • Loose Ties at Blackwall Hitch
    venue: Blackwall Hitch

    Join us for a live performance from Loose Ties on Saturday, July 22nd at 9:30pm! ...

  • Bottomless Bloody Mary Bar at Rams Head Tavern
    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 at Rams Head Tavern
    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 at Killarney House
    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 at Brian Boru
    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 Roadhouse
    venue: Rams Head Roadhouse

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

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

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

  • Sunday Brunch at Rams Head Dockside
    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! ...

  • Sunday Gospel in the Park
    venue: Whitmore Park

    Join us on Sunday evening for Sunday Gospel In the Park Night, featuring free concerts of local gospel singing groups.  June 11 - Chozen G ...

  • Sunday Jazz Brunch at Blackwall Hitch
    venue: Blackwall Hitch

    Join us for a brunch buffet and a live jazz performance from Sly 45!  ...