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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Fall Classics: A Concert for Peace

Saturday • 7:30 PM

Maryland Hall

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Sex Offender Interview Specialist Course - October 2026

Monday • 8:00 AM

Westin Annapolis

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Meet & Greet at Market House Rise Up Coffee with Jessica Haire

Thu, Oct 15 • 8:15 AM

Rise Up Coffee - City Dock

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Ballet Theatre of Maryland presents "La Sylphide"

Sun, Oct 18 • 2:00 PM

Maryland Hall

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Halloween Spooktacular!

Sun, Oct 25 • 3:00 PM

St. John's College

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Paint & Sip

Sun, Oct 25 • 2:00 PM

Middleton Tavern

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Artamotive: Cool Car Paintings Featuring Works by Cindy Fletcher-Holden

Sat, Nov 7 • 5:00 PM

Jo Fleming Contemporary Art Gallery

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SAME Mid-Maryland Industry Day: Mission-Critical Infrastructure Resilience

Wed, Jan 20 • 8:00 AM

Mahan Hall

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Fall Classics: A Concert for Peace

Saturday • 7:30 PM

Maryland Hall

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Sex Offender Interview Specialist Course - October 2026

Monday • 8:00 AM

Westin Annapolis

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Meet & Greet at Market House Rise Up Coffee with Jessica Haire

Thu, Oct 15 • 8:15 AM

Rise Up Coffee - City Dock

Check ticket price on event

Ballet Theatre of Maryland presents "La Sylphide"

Sun, Oct 18 • 2:00 PM

Maryland Hall

Check ticket price on event

Halloween Spooktacular!

Sun, Oct 25 • 3:00 PM

St. John's College

Check ticket price on event

Paint & Sip

Sun, Oct 25 • 2:00 PM

Middleton Tavern

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Artamotive: Cool Car Paintings Featuring Works by Cindy Fletcher-Holden

Sat, Nov 7 • 5:00 PM

Jo Fleming Contemporary Art Gallery

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SAME Mid-Maryland Industry Day: Mission-Critical Infrastructure Resilience

Wed, Jan 20 • 8:00 AM

Mahan Hall

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Online Events

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How To Be Kind To Yourself - Shahroo Izadi

Wednesday • 7:00 PM GMT+1

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HBR Press Webinar: Resilient Optimism

Thu, Oct 15 • 8:00 AM EDT

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HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

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Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

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(WATCH ONLINE) Dr. Jonathan Sarna with Joseph Weisberg

Tue, Oct 27 • 6:30 PM EDT

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Witch hunts and real lives

Fri, Oct 30 • 2:00 PM GMT

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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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How To Be Kind To Yourself - Shahroo Izadi

Wednesday • 7:00 PM GMT+1

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HBR Press Webinar: Resilient Optimism

Thu, Oct 15 • 8:00 AM EDT

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HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

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Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

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(WATCH ONLINE) Dr. Jonathan Sarna with Joseph Weisberg

Tue, Oct 27 • 6:30 PM EDT

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Witch hunts and real lives

Fri, Oct 30 • 2:00 PM GMT

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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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This Weekend

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Dancing Night at Caliente Grill - Class & Social Dance

Tomorrow • 7:00 PM

Caliente Grill

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

Tomorrow • 7:00 PM + 2 more

Marmo Annapolis

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Annapolis Naval Intelligence Mission

Tomorrow • 4:00 PM + 8 more

Susan Campbell Park

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Harbor Hustle

Tomorrow • 4:00 PM + 8 more

1 Dock St

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Fall Classics: A Concert for Peace

Saturday • 7:30 PM

Maryland Hall

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⁠Mindful Wellness Walk in Annapolis

Saturday • 11:00 AM + 3 more

Brown Mustache Coffee, LLC

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Unlock the codes that are hidden inside your birth chart!

Sunday • 1:00 PM

Annapolis Crystals

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Dancing Night at Caliente Grill - Class & Social Dance

Tomorrow • 7:00 PM

Caliente Grill

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

Tomorrow • 7:00 PM + 2 more

Marmo Annapolis

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Annapolis Naval Intelligence Mission

Tomorrow • 4:00 PM + 8 more

Susan Campbell Park

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Harbor Hustle

Tomorrow • 4:00 PM + 8 more

1 Dock St

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Fall Classics: A Concert for Peace

Saturday • 7:30 PM

Maryland Hall

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⁠Mindful Wellness Walk in Annapolis

Saturday • 11:00 AM + 3 more

Brown Mustache Coffee, LLC

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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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ITZALL Goode and SHC Music Tribe Present Pete Best and Dana Cooper

Mon, Oct 19 • 7:30 PM

49 West Coffeehouse, Winebar & Gallery

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

Fri, Oct 30 • 7:00 PM

Metropolitan Kitchen & Lounge

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The Good Times Experience

Sat, Nov 14 • 8:00 PM

Metropolitan Kitchen & Lounge

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Landscapes of Radiance & Light

Sat, Jun 5 • 7:30 PM

Maryland Hall

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ITZALL Goode and SHC Music Tribe Present Pete Best and Dana Cooper

Mon, Oct 19 • 7:30 PM

49 West Coffeehouse, Winebar & Gallery

Check ticket price on event

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

Fri, Oct 30 • 7:00 PM

Metropolitan Kitchen & Lounge

Check ticket price on event

The Good Times Experience

Sat, Nov 14 • 8:00 PM

Metropolitan Kitchen & Lounge

Check ticket price on event

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.