Best events in
Annapolis

From midweek gatherings on West Street to bustling weekends downtown, there are always events and things to do in Annapolis, MD. The city's historic, walkable core makes it easy to move between intimate music venues, theaters, and lively restaurants. Meanwhile, the maritime community of Eastport offers a more relaxed pace with its own respected waterfront dining scene.

Start an evening in the Arts District on West Street, which hosts the monthly Monthly Arts Festival and the seasonal Dinner Under the Stars series.
Find intimate concerts and comedy shows from touring acts at Rams Head On Stage, located in the Historic District.
Experience classical music with the Annapolis Symphony Orchestra at Maryland Hall or catch a stage production at the Classic Theatre of Maryland.

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Popular in Annapolis

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BikeAAA 2026 Annual Meeting

Thu, Nov 12 • 6:00 PM

Metropolitan Kitchen & Lounge

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Laughs in the Lounge

Fri, Nov 13 • 7:00 PM

Stan & Joe's Saloon

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The Resin Room - One Year Anniversary Celebration

Sat, Nov 14 • 2:00 PM

The Resin Room

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Ari Hest at 49 West in Annapolis, MD

Mon, Nov 16 • 7:30 PM

49 West Coffeehouse, Winebar & Gallery

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Bosch Best Practices | Beltsville

Tue, Nov 17 • 8:00 AM

Johnstone Supply Annapolis

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Speaking Truth to Power: The Free Press in a Changing World

Wed, Nov 18 • 5:00 PM

Maryland Hall

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Encore ROCKS Annapolis Concert

Sun, Dec 6 • 7:00 PM

Maryland Hall

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Ballet Theatre of Maryland presents "The Nutcracker"

Sun, Dec 13 • 1:00 PM

Maryland Hall

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BikeAAA 2026 Annual Meeting

Thu, Nov 12 • 6:00 PM

Metropolitan Kitchen & Lounge

Check ticket price on event

Laughs in the Lounge

Fri, Nov 13 • 7:00 PM

Stan & Joe's Saloon

Check ticket price on event

The Resin Room - One Year Anniversary Celebration

Sat, Nov 14 • 2:00 PM

The Resin Room

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Ari Hest at 49 West in Annapolis, MD

Mon, Nov 16 • 7:30 PM

49 West Coffeehouse, Winebar & Gallery

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Bosch Best Practices | Beltsville

Tue, Nov 17 • 8:00 AM

Johnstone Supply Annapolis

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Speaking Truth to Power: The Free Press in a Changing World

Wed, Nov 18 • 5:00 PM

Maryland Hall

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Encore ROCKS Annapolis Concert

Sun, Dec 6 • 7:00 PM

Maryland Hall

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Ballet Theatre of Maryland presents "The Nutcracker"

Sun, Dec 13 • 1:00 PM

Maryland Hall

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Online Events

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Humanitarian Water Engineering Fall 2026

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

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REVISED Cottage Food Safety Statewide Online Training

Fri, Nov 13 • 9:00 AM MST

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Gestion de l’anxiété dans le traitement des troubles alimentaires

Fri, Nov 13 • 1:00 PM EST

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The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Humanitarian Water Engineering Fall 2026

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

Check ticket price on event

The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

Check ticket price on event

REVISED Cottage Food Safety Statewide Online Training

Fri, Nov 13 • 9:00 AM MST

Check ticket price on event

Gestion de l’anxiété dans le traitement des troubles alimentaires

Fri, Nov 13 • 1:00 PM EST

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The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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This Weekend

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Crafts & Coffee: Ceremony x Mia Moon

Tomorrow • 6:00 PM

Ceremony Coffee Roasters - Roastery

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The Witching Hour: Mystery & Mirth

Tomorrow • 6:30 PM

172 Green St

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The Witching Hour: Mystery & Mirth

Tomorrow • 6:30 PM

172 Green St

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Dream Punch, Light Beams, PLRLS, Chain Puller at Metropolitan

Tomorrow • 7:00 PM

Metropolitan Kitchen & Lounge

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Co-Founder: Dinner with Entrepreneurs - Annapolis: Dinner for a Cause

Tomorrow • 7:00 PM + 1 more

Marmo Annapolis

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Le Petit Masquerade @ Rumhouse (Caribbean Fine Dining - Annapolis)

Saturday • 6:00 PM

Rumhouse

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Unlock the codes that are hidden inside your birth chart!

Sunday • 1:00 PM

Annapolis Crystals

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Crafts & Coffee: Ceremony x Mia Moon

Tomorrow • 6:00 PM

Ceremony Coffee Roasters - Roastery

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The Witching Hour: Mystery & Mirth

Tomorrow • 6:30 PM

172 Green St

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The Witching Hour: Mystery & Mirth

Tomorrow • 6:30 PM

172 Green St

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Dream Punch, Light Beams, PLRLS, Chain Puller at Metropolitan

Tomorrow • 7:00 PM

Metropolitan Kitchen & Lounge

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Co-Founder: Dinner with Entrepreneurs - Annapolis: Dinner for a Cause

Tomorrow • 7:00 PM + 1 more

Marmo Annapolis

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Le Petit Masquerade @ Rumhouse (Caribbean Fine Dining - Annapolis)

Saturday • 6:00 PM

Rumhouse

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Unlock the codes that are hidden inside your birth chart!

Sunday • 1:00 PM

Annapolis Crystals

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Music events

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The Good Times Experience

Sat, Nov 14 • 8:00 PM

Metropolitan Kitchen & Lounge

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Ari Hest at 49 West in Annapolis, MD

Mon, Nov 16 • 7:30 PM

49 West Coffeehouse, Winebar & Gallery

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Encore ROCKS Annapolis Concert

Sun, Dec 6 • 7:00 PM

Maryland Hall

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Landscapes of Radiance & Light

Sat, Jun 5 • 7:30 PM

Maryland Hall

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The Good Times Experience

Sat, Nov 14 • 8:00 PM

Metropolitan Kitchen & Lounge

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Ari Hest at 49 West in Annapolis, MD

Mon, Nov 16 • 7:30 PM

49 West Coffeehouse, Winebar & Gallery

Check ticket price on event

Encore ROCKS Annapolis Concert

Sun, Dec 6 • 7:00 PM

Maryland Hall

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Landscapes of Radiance & Light

Sat, Jun 5 • 7:30 PM

Maryland Hall

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Points of Interest near Annapolis

Annapolis Maritime Museum Park

Banneker Douglass Museum

Pirate Adventures On The Chesapeake

William Paca House Garden

Watermark Tours Charters Cruises

Annapolis City Dock

Frequently asked questions about Annapolis

Where can I find live music events in Annapolis?

Rams Head On Stage is a top spot for touring acts across many genres. For a more casual vibe, local pubs like Stan & Joe's Saloon on West Street regularly feature area bands. The downtown area's walkability makes it easy to discover music while exploring different venues.

What are some notable art events in the Annapolis Arts District?

The West Street Arts District is a hub for creative happenings. It hosts the Monthly Arts Festival, a large monthly market from May through November. The area also features unique spaces like Prism Annapolis, which showcases local art during its public events.

Are there good date night ideas in downtown Annapolis?

The walkable downtown offers many choices for a memorable evening. Consider a play at The Colonial Players or the Classic Theatre of Maryland, followed by a stroll through the Historic District. Many restaurants along Main Street transition into lively spots for a late-night drink.

What kind of outdoor events happen in Annapolis?

Annapolis hosts many popular outdoor gatherings, especially in warmer months. The Annapolis Town Center Summer Concerts are a recurring favorite. In the fall, the city is known for its major in-water boat shows at the City Dock, a signature local event.

How can I experience the local food and drink scene?

West Street's Dinner Under the Stars is a celebrated weekly event from May through September where restaurants offer al fresco dining. For locally sourced goods, visit the Anne Arundel County Farmers' Market, which operates year-round on Sundays, with additional market days seasonally.

Where are free things to do in Annapolis?

Many community events in Annapolis are free to attend. Strolling through the Monthly Arts Festival on West Street is a great way to see local art. The Annapolis Town Center Summer Concerts also offer free outdoor performances for the public to enjoy.

Is there a venue for comedy shows in Annapolis?

Rams Head On Stage frequently features touring stand-up comedians. This intimate venue in the Historic District is known for bringing national comedy acts to the city. The schedule often includes comedy performances alongside its regular music programming.

What is the nightlife like in Annapolis?

The city's nightlife centers on the highly walkable Historic District and Main Street. Restaurants often become lively bars as the evening progresses. For a more relaxed scene, the Eastport neighborhood offers waterfront spots with a genuine maritime community feel across the bridge.