Best events in
Earleville

Looking for events or things to do in Earleville, MD? The local scene is deeply tied to its seasons, with outdoor festivals and waterfront music flourishing from spring through fall. Nearby towns like Chesapeake City offer lively evenings by the C&D Canal, while North East provides a classic Main Street atmosphere.

An evening in Chesapeake City often means watching ships pass through the C&D Canal before settling in for dinner and live music at a waterfront spot like the Chesapeake Inn or Schaefer's Canal House.
Step back in time at Mount Harmon Plantation, a historic site that hosts annual events like a Colonial Festival and spring Point to Point Races.
Find community gatherings and performances in North East, from the monthly 2nd Fridays on Main music series to shows at the Milburn Stone Theatre.

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Towson

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Crownsville

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Millersville

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Bel Air

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Linthicum

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Cockeysville

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Thu, Oct 15 • 1:00 PM GMT+1

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Thu, Oct 22 • 6:00 PM GMT+2

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Tue, Oct 27 • 11:30 AM EDT

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Thu, Nov 5 • 1:00 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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Today • 7:30 PM GMT+1

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Tomorrow • 6:00 PM EDT

Check ticket price on event

HBR Press Webinar: Resilient Optimism

Thu, Oct 15 • 8:00 AM EDT

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Thu, Oct 15 • 1:00 PM GMT+1

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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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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Events near Earleville

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Fall Stained Glass 6-Week Series: Morning Course

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Sat, Oct 24 • 3:00 PM

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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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Black & White Noir Nights Masquerade Ball

Fri, Nov 6 • 8:00 PM

Bulle Rock Golf Course

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The Party of the Year: GATSBY

Fri, Nov 13 • 8:30 PM

Chesapeake Inn Restaurant & Marina

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Fall Stained Glass 6-Week Series: Morning Course

Gibby Center for the Arts

Check ticket price on event

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Sat, Oct 17 • 12:00 PM

Fairfield Inn & Suites

Check ticket price on event

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Fri, Oct 23 • 6:30 PM

Filasky's Produce/Farm

Check ticket price on event

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Sat, Oct 24 • 3:00 PM

Westown Movies

Check ticket price on event

Waterfowl and Foliage Public Paddle - 2026- Sultana Education Foundation

Sun, Oct 25 • 10:00 AM

Rileys Mill Landing

Check ticket price on event

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

Fri, Oct 30 • 2:30 PM

Chestertown Marina

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

The Party of the Year: GATSBY

Fri, Nov 13 • 8:30 PM

Chesapeake Inn Restaurant & Marina

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Frequently asked questions about Earleville

Where can I find live music events near Earleville?

Chesapeake City's waterfront is a top destination for live music. Venues like Chesapeake Inn Restaurant & Marina and Schaefer's Canal House have regular performances, especially on their outdoor decks. In Elkton, the Elkton Music Hall presents a mix of rock and folk acts.

What are some good date night ideas in the Earleville area?

A trip to Broken Spoke Winery offers a great date night setting. The farm winery frequently hosts live music and food trucks in a relaxed, rural atmosphere. For a different vibe, an evening in Chesapeake City combining dinner with a stroll along the canal is a popular choice.

Are there family-friendly events in the Earleville region?

The annual Cecil County Fair is a classic family-friendly event. Held each summer, it features a carnival, tractor pulls, and a rodeo. For a historical outing, Mount Harmon Plantation hosts living history demonstrations that appeal to all ages.

What kind of outdoor events happen near Earleville?

Outdoor events often take place at scenic and historic locations. Mount Harmon Plantation hosts the annual Point to Point horse races each spring. The Farm to Table Farmers Market in Chesapeake City is another great seasonal outdoor gathering on Saturdays from May to October.

What is the event scene like in Chesapeake City?

The scene in Chesapeake City revolves around its canal-side location. Evenings feature a relaxed rhythm of watching ships, waterfront dining, and listening to live music. The town’s historic charm also makes it a hub for boutique shopping and social gatherings.

How can I find free events to attend near Earleville?

Exploring the town of North East is a good way to find free activities. The monthly 2nd Fridays on Main event brings free live music to the streets. The Farm to Table Farmers Market in Chesapeake City also offers free admission for browsing local goods.

What kinds of cultural events happen in the area?

The Milburn Stone Theatre is a central hub for cultural events. Located on the Cecil College campus, its calendar includes community theatre, concerts, and film screenings. The theatre also hosts an annual Celtic Festival each March celebrating Irish culture.

What's the nightlife like around Earleville?

Nightlife in the region is focused on relaxed dining and live music. Chesapeake City's waterfront restaurants provide a lively atmosphere without being a late-night club scene. Evenings tend to center around enjoying the scenic views of the C&D Canal with a meal and entertainment.

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Nearby cities

Baltimore

Wilmington

Annapolis

Lancaster

Towson

Crownsville

Middletown

Catonsville

Bel Air South

Glen Burnie

Dover

Owings Mills

Woodlawn

Timonium

West Chester

Millersville

Arbutus

Odenton

Pleasant Hills

Dundalk

Pikesville

Newark

Bel Air

Linthicum

Cockeysville

Millville

Parkville

Vineland

Severna Park

Ellicott City

Baltimore

Wilmington

Annapolis

Lancaster

Towson

Crownsville

Middletown

Catonsville

Bel Air South

Glen Burnie

Dover

Owings Mills

Woodlawn

Timonium

West Chester

Millersville

Arbutus

Odenton

Pleasant Hills

Dundalk

Pikesville

Newark

Bel Air

Linthicum

Cockeysville

Millville

Parkville

Vineland

Severna Park

Ellicott City

Online Events

A Norman stitch-up? The story behind the Bayeux Tapestry

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(ONLINE) Women on the Move with Ann Patchett

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

Washington Crossing the Delaware / The Crossing - Film History Livestream

A Norman stitch-up? The story behind the Bayeux Tapestry

AI Animation Studio: Create Kids' Cartoons

HBR Press Webinar: Resilient Optimism

HBR Book Webinar: Resilient Optimism

Coming Together for Multilingual Children with DLD

(ONLINE) Women on the Move with Ann Patchett

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

Washington Crossing the Delaware / The Crossing - Film History Livestream