Best events in
Charlestown

While it has a reputation for being quiet, there are plenty of community events and things to do in Charlestown, MD. The town's social calendar is rooted in its waterfront setting along the North East River and its well-preserved Historic District. Community gatherings, from outdoor concerts to annual festivals, are a cornerstone of local life.

Walk through the Charlestown Historic District, where colonial-era buildings set the scene for quiet outings and occasional open houses at The 107 House.
Catch live performances and community festivals at Avalon Park & Stage, the town's central hub for outdoor entertainment.
Look for annual traditions like the Rockfish Music and Arts Festival or the town-wide Community Yard Sale that bring neighbors together.

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Events near Charlestown

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"Spooky" Craft Night

Fri, Oct 16 • 6:00 PM

Gibby Center for the Arts

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How to Network for Small Business Owners

Sat, Oct 17 • 12:00 PM

Fairfield Inn & Suites

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Black & White Noir Nights Masquerade Ball

Fri, Nov 6 • 8:00 PM

Bulle Rock Golf Course

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Purrs and Pints: A Chesapeake Feline Association Music Bingo Fundraiser

Fri, Nov 6 • 6:30 PM

Hopkins Farm Brewery

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Justice for Chris Harper

Sun, Nov 8 • 2:00 PM

300 W Main St

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The Party of the Year: GATSBY

Fri, Nov 13 • 8:30 PM

Chesapeake Inn Restaurant & Marina

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2026 Annual Louis L. Redding Benefit & Awards Gala

Fri, Nov 13 • 6:00 PM

Deerfield Golf Course

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Wine Tasting Class: Wines for the Holidays

Wed, Dec 2 • 6:00 PM

Casa Carmen Farm and Winery

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"Spooky" Craft Night

Fri, Oct 16 • 6:00 PM

Gibby Center for the Arts

Check ticket price on event

How to Network for Small Business Owners

Sat, Oct 17 • 12:00 PM

Fairfield Inn & Suites

Check ticket price on event

Black & White Noir Nights Masquerade Ball

Fri, Nov 6 • 8:00 PM

Bulle Rock Golf Course

Check ticket price on event

Purrs and Pints: A Chesapeake Feline Association Music Bingo Fundraiser

Fri, Nov 6 • 6:30 PM

Hopkins Farm Brewery

Check ticket price on event

Justice for Chris Harper

Sun, Nov 8 • 2:00 PM

300 W Main St

Check ticket price on event

The Party of the Year: GATSBY

Fri, Nov 13 • 8:30 PM

Chesapeake Inn Restaurant & Marina

Check ticket price on event

2026 Annual Louis L. Redding Benefit & Awards Gala

Fri, Nov 13 • 6:00 PM

Deerfield Golf Course

Check ticket price on event

Wine Tasting Class: Wines for the Holidays

Wed, Dec 2 • 6:00 PM

Casa Carmen Farm and Winery

Check ticket price on event

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Online Events

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HBR Book Webinar: Resilient Optimism

Thursday • 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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Biodiversity Law and Governance Day 2026

Sat, Oct 24 • 11:30 AM GMT+4

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM 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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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

Check ticket price on event

Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

Check ticket price on event

Biodiversity Law and Governance Day 2026

Sat, Oct 24 • 11:30 AM GMT+4

Check ticket price on event

(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

Check ticket price on event

Witch hunts and real lives

Fri, Oct 30 • 2:00 PM GMT

Check ticket price on event

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

Thu, Nov 5 • 1:00 PM GMT

Check ticket price on event

Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

Check ticket price on event

Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

Check ticket price on event

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Frequently asked questions about Charlestown

Are there live music events in Charlestown?

Avalon Park & Stage is the main venue for live music events in town. It hosts the summer Music in the Park series and is a key feature of the annual Rockfish Music and Arts Festival. The Wellwood restaurant also hosts occasional musical performances.

What are some family-friendly things to do in Charlestown?

Families can enjoy outdoor events and festivals at Avalon Park. This waterfront space hosts community gatherings like the annual Rockfish Music and Arts Festival, which features activities for kids, and the early July Fourth of July Celebration with food and music.

Where can I find outdoor events in Charlestown?

Avalon Park is the center for outdoor community events in town. The waterfront park hosts the Music in the Park concert series, the annual Rockfish Music and Arts Festival, and the local Fourth of July Celebration. Its green lawns are perfect for community gatherings.

What is there to do in the Charlestown Historic District?

The Historic District offers a look into the town's colonial past. Visitors can take a walking tour of the preserved architecture or attend the public open house at The 107 House (Tory House) on the monthly of each month from May through October.

How can I find free events in Charlestown, MD?

Many community events in Charlestown are free to attend. The Music in the Park series at Avalon Park & Stage offers free concerts, and strolling through the historic district or enjoying the waterfront views is always a no-cost activity.

What annual events happen in Charlestown?

Charlestown hosts several beloved annual community events. The Rockfish Music and Arts Festival brings live music and vendors to Avalon Park each September, while the town-wide Community Yard Sale happens in late spring. The town also holds a popular Fourth of July Celebration.

What are some date night ideas in Charlestown?

A classic Charlestown date involves dinner at a waterfront restaurant like The Wellwood. The restaurant sometimes features live music, and a walk along the North East River or through the quiet, tree-lined Historic District can complete the evening.

Is there much nightlife in Charlestown?

Charlestown's nightlife is very quiet and centers on relaxed evenings. A waterfront meal at The Wellwood is a popular option, but for more lively bars and a wider range of evening events, people often visit nearby towns like North East or Elkton.

Events near Charlestown

"Spooky" Craft Night

How to Network for Small Business Owners

Black & White Noir Nights Masquerade Ball

Purrs and Pints: A Chesapeake Feline Association Music Bingo Fundraiser

Justice for Chris Harper

The Party of the Year: GATSBY

2026 Annual Louis L. Redding Benefit & Awards Gala

Wine Tasting Class: Wines for the Holidays

"Spooky" Craft Night

How to Network for Small Business Owners

Black & White Noir Nights Masquerade Ball

Purrs and Pints: A Chesapeake Feline Association Music Bingo Fundraiser

Justice for Chris Harper

The Party of the Year: GATSBY

2026 Annual Louis L. Redding Benefit & Awards Gala

Wine Tasting Class: Wines for the Holidays

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Nearby cities

Baltimore

Philadelphia

Wilmington

Lancaster

Towson

Catonsville

Middletown

Glen Burnie

Annapolis

Bel Air South

York

King of Prussia

Dover

Owings Mills

Timonium

Millersville

Woodlawn

West Chester

Arbutus

Dundalk

Pleasant Hills

Pikesville

Cockeysville

Newark

Bel Air

Linthicum

Pottstown

Parkville

Severna Park

Chester

Baltimore

Philadelphia

Wilmington

Lancaster

Towson

Catonsville

Middletown

Glen Burnie

Annapolis

Bel Air South

York

King of Prussia

Dover

Owings Mills

Timonium

Millersville

Woodlawn

West Chester

Arbutus

Dundalk

Pleasant Hills

Pikesville

Cockeysville

Newark

Bel Air

Linthicum

Pottstown

Parkville

Severna Park

Chester