Best events in
Chestertown

Looking for events or things to do in Chestertown, MD? The town's social life revolves around its walkable historic downtown, where 18th-century architecture meets a lively arts scene along the Chester River. This historic port town maintains a relaxed community pace, punctuated by popular recurring festivals and monthly art walks.

Explore the historic downtown Arts & Entertainment District, where a stroll can lead to a gallery opening during the monthly Monthly celebration or a play at the Garfield Center for the Arts.
Catch live music and enjoy wood-fired pizza at Bad Alfred's, a popular downtown brewpub and distillery that offers a lively atmosphere.
Find community festivals and outdoor performances set against the backdrop of the Chester River at the scenic Wilmer Park.

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Popular in Chestertown

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World Migratory Bird Day for Chestertown & Washington College

Saturday • 7:45 AM

Semans-Griswold Environmental Hall at Washington College

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Understanding the story. Building Hope. Creating Connections.

Tuesday • 6:00 PM

Minary’s Dream Alliance, Inc.

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Richard O'Brien's The Rocky Horror Show

Fri, Oct 16 • 8:00 PM + 8 more

Garfield Center for the Arts at the Prince Theatre

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Autism Family Fun & Resource Day

Fri, Oct 16 • 12:00 PM

Kent County Public Library

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2026 Sultana Downrigging Festival Music Village Passes

Chestertown Marina

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2026 Downrigging Tall Ship Sails: SUNDAY NOV 1, 1:00pm-3:30pm

Sun, Nov 1 • 1:00 PM

Chestertown Marina

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Learn to Play American MahJong-A 3 Part Series: Nov. 8, 15, 22

Sun, Nov 8 • 11:00 AM

Lawrence Wetlands Preserve

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Paint & Sip

Sat, Nov 21 • 2:00 PM

Sumner Hall

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World Migratory Bird Day for Chestertown & Washington College

Saturday • 7:45 AM

Semans-Griswold Environmental Hall at Washington College

Check ticket price on event

Understanding the story. Building Hope. Creating Connections.

Tuesday • 6:00 PM

Minary’s Dream Alliance, Inc.

Check ticket price on event

Richard O'Brien's The Rocky Horror Show

Fri, Oct 16 • 8:00 PM + 8 more

Garfield Center for the Arts at the Prince Theatre

Check ticket price on event

Autism Family Fun & Resource Day

Fri, Oct 16 • 12:00 PM

Kent County Public Library

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2026 Sultana Downrigging Festival Music Village Passes

Chestertown Marina

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2026 Downrigging Tall Ship Sails: SUNDAY NOV 1, 1:00pm-3:30pm

Sun, Nov 1 • 1:00 PM

Chestertown Marina

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Learn to Play American MahJong-A 3 Part Series: Nov. 8, 15, 22

Sun, Nov 8 • 11:00 AM

Lawrence Wetlands Preserve

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Paint & Sip

Sat, Nov 21 • 2:00 PM

Sumner Hall

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Online Events

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AI Animation Studio: Create Kids' Cartoons

Today • 6:00 PM EDT

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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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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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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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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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AI Animation Studio: Create Kids' Cartoons

Today • 6:00 PM EDT

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HBR Press Webinar: Resilient Optimism

Thu, Oct 15 • 8:00 AM EDT

Check ticket price on event

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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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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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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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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Free events

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World Migratory Bird Day for Chestertown & Washington College

Saturday • 7:45 AM

Semans-Griswold Environmental Hall at Washington College

Check ticket price on event

Understanding the story. Building Hope. Creating Connections.

Tuesday • 6:00 PM

Minary’s Dream Alliance, Inc.

Check ticket price on event

Autism Family Fun & Resource Day

Fri, Oct 16 • 12:00 PM

Kent County Public Library

Check ticket price on event

Sustainable Farming

Thu, Nov 19 • 6:00 PM

Sultana's Holt Center

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World Migratory Bird Day for Chestertown & Washington College

Saturday • 7:45 AM

Semans-Griswold Environmental Hall at Washington College

Check ticket price on event

Understanding the story. Building Hope. Creating Connections.

Tuesday • 6:00 PM

Minary’s Dream Alliance, Inc.

Check ticket price on event

Autism Family Fun & Resource Day

Fri, Oct 16 • 12:00 PM

Kent County Public Library

Check ticket price on event

Sustainable Farming

Thu, Nov 19 • 6:00 PM

Sultana's Holt Center

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From nearby cities

Dueling Pianos at Waterman's Crab House - Dinner & Show

Sunday • 6:00 PM

Waterman's Crab House, West Sharp Street, Rock Hall, MD, USA

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Grape Expectations: Brampton 1860 “Autumn in Full Swing: A Harvest Supper”

Thu, Oct 15 • 6:00 PM

25227 Chestertown Rd

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Landing Strip Paint Night

Mon, Oct 19 • 6:00 PM

The Landing Strip

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Waterfowl and Foliage Public Paddle - 2026- Sultana Education Foundation

Sun, Oct 25 • 10:00 AM

Rileys Mill Landing

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2026 Downrigging Tall Ship Sails: FRIDAY OCT 30, 2:30pm-5:00pm

Fri, Oct 30 • 2:30 PM

Chestertown Marina

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2026 Sultana Downrigging Festival Music Village Passes

Chestertown Marina

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Black & White Noir Nights Masquerade Ball

Fri, Nov 6 • 8:00 PM

Bulle Rock Golf Course

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2026 Queen Anne's County Harvest Breakfast

Fri, Nov 13 • 7:30 AM

Chesapeake College - Caroline Center

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Dueling Pianos at Waterman's Crab House - Dinner & Show

Sunday • 6:00 PM

Waterman's Crab House, West Sharp Street, Rock Hall, MD, USA

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Grape Expectations: Brampton 1860 “Autumn in Full Swing: A Harvest Supper”

Thu, Oct 15 • 6:00 PM

25227 Chestertown Rd

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Landing Strip Paint Night

Mon, Oct 19 • 6:00 PM

The Landing Strip

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Waterfowl and Foliage Public Paddle - 2026- Sultana Education Foundation

Sun, Oct 25 • 10:00 AM

Rileys Mill Landing

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2026 Downrigging Tall Ship Sails: FRIDAY OCT 30, 2:30pm-5:00pm

Fri, Oct 30 • 2:30 PM

Chestertown Marina

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2026 Sultana Downrigging Festival Music Village Passes

Chestertown Marina

Check ticket price on event

Black & White Noir Nights Masquerade Ball

Fri, Nov 6 • 8:00 PM

Bulle Rock Golf Course

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2026 Queen Anne's County Harvest Breakfast

Fri, Nov 13 • 7:30 AM

Chesapeake College - Caroline Center

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Points of Interest near Chestertown

Massoniart Gallery

Frequently asked questions about Chestertown

Where are the best spots for live music events in Chestertown?

Bad Alfred's is a go-to spot for live music in a brewpub setting. The downtown distillery offers craft cocktails and wood-fired pizza alongside local performers. The annual Chestertown Jazz Festival also brings national and regional performers to the waterfront.

What are some highlights of the arts and culture scene in Chestertown?

The downtown Arts & Entertainment District is the center of Chestertown's creative scene. The monthly Monthly event features gallery openings and late hours at local shops. For performing arts, the Garfield Center for the Arts stages plays and concerts.

Are there family-friendly events in Chestertown?

Many community celebrations in Chestertown are great for all ages. The annual Chestertown Tea Party Festival, held over Memorial Day weekend, includes reenactments and a parade. Wilmer Park also hosts various outdoor events with space for families by the river.

What kind of food and drink events can be found in Chestertown?

The Chestertown Farmers' & Artisans' Market is a key weekly food event. Held every Saturday, it's a place to find local produce, baked goods, and crafts. For a spirited experience, Bad Alfred's offers distillery tours alongside its food and drink menu.

How can I find free events to attend in Chestertown?

Exploring the historic downtown during Monthly is a popular free activity. Galleries and shops welcome visitors with special openings, often with street music. Many rehearsals for the National Music Festival are also open to the public at no cost.

What are some good date night ideas in Chestertown?

A classic Chestertown date can start with drinks and oysters at The Retriever Bar. From there, it's an easy walk to catch a performance at the Garfield Center for the Arts. For a more secretive vibe, find the green light at Zelda's Speakeasy.

Where can I find outdoor events in Chestertown?

Wilmer Park is the primary venue for outdoor community events and festivals. Situated along the Chester River, it provides a scenic setting for concerts and gatherings. The downtown farmers' market is another consistent outdoor social hub held every Saturday.

What is the nightlife like in downtown Chestertown?

Chestertown's nightlife is relaxed and centered around its downtown pubs and bars. Spots like Blue Bird Tavern offer a casual atmosphere with pool tables and sports. For a cozy, intimate experience, locals frequent the hidden Zelda's Speakeasy.