Best events in
Gloucester

Looking for events or things to do in Gloucester, VA? The area's character is defined by the lively, historic Main Street village, which serves as a central hub for a community that values its quiet, waterfront surroundings. A relaxed pace of life marks the day-to-day, while annual festivals and monthly gatherings punctuate the calendar with creative energy.

A typical outing on Main Street might involve exploring the galleries and shops during a Monthly art walk before grabbing a drink at Gloucester Brewing Company.
Live music finds a home at intimate venues like Flat Iron Crossroads, which hosts a diverse range of genres throughout the year.
For a change of scenery, Under the Stars Farm offers seasonal events like hands-on workshops and farm-to-table dinners in a unique agricultural setting.

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Urbanna

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Bellwood

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Waverly

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Events near Gloucester

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Exhibit Hall- 2026 Virginia Council for the Social Studies Conference

Today • 4:00 PM

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Presidents Heads Evening Photo Shoot & Light Painting Workshop

Saturday • 7:00 PM

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Michael Ray Concert at Riverwalk Landing

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A Lesson inTarot Card Reading

Sun, Oct 18 • 6:00 PM

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Sat, Oct 24 • 2:00 PM

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Candlelight Dinner With Edgar Allan Poe

Fri, Oct 30 • 6:00 PM

Shields Tavern

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October Cookie Decorating Class

Fri, Oct 30 • 6:00 PM

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2027 William & Mary Law School Negotiation Tournament

Fri, Feb 26 • 8:30 AM

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Exhibit Hall- 2026 Virginia Council for the Social Studies Conference

Today • 4:00 PM

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Presidents Heads Evening Photo Shoot & Light Painting Workshop

Saturday • 7:00 PM

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Check ticket price on event

Michael Ray Concert at Riverwalk Landing

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Riverwalk Landing

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Sun, Oct 18 • 6:00 PM

Tabitha Sewer Studio

Check ticket price on event

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Sat, Oct 24 • 2:00 PM

Kimball Theatre

Check ticket price on event

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Fri, Oct 30 • 6:00 PM

Shields Tavern

Check ticket price on event

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Fri, Oct 30 • 6:00 PM

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Check ticket price on event

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Frequently asked questions about Gloucester

Where can I find live music events in Gloucester?

Flat Iron Crossroads is a premier destination for live music in an intimate setting. The venue attracts a diverse lineup of musical acts, and Gloucester Brewing Company also frequently hosts local musicians, especially on weekends.

What defines the art scene in Gloucester?

The local art scene is centered around the galleries on Main Street. Arts on Main serves as a community hub with rotating exhibits, while the monthly First Fridays event invites everyone to explore new art. The annual Gloucester Arts Festival also showcases local talent.

Are there popular family-friendly events in Gloucester?

The Gloucester Daffodil Festival is a major annual event perfect for all ages. This street fair celebrates local heritage with a parade and vendors. The summer Concerts on the Green series also offers a great, relaxed outing for families.

How can I find free events to attend?

Many community gatherings in Gloucester are free to attend. The Concerts on the Green series provides free outdoor music in the summer, and the monthly First Fridays art walk along Main Street is another popular free event.

What are some notable food and drink events?

Gloucester Brewing Company is a social hub with regular trivia, music bingo, and food trucks. For something different, Under the Stars Farm hosts seasonal farm-to-table dinners and other culinary workshops in a rustic setting.

Can you suggest a date night idea on Main Street?

A great date night could start with an art-focused stroll through Main Street Village. Visiting Arts on Main or the Fine Arts Museum of Gloucester before heading to a local restaurant creates a memorable evening, especially during a First Fridays event.

Which venues host unique outdoor events?

Under the Stars Farm offers seasonal you-pick lavender and hands-on workshops. Additionally, the Gloucester Farmers Market, held monthly from May into the fall at Ware Episcopal Church, provides an open-air experience with local goods and entertainment.

What is the event scene like in the Main Street village?

The Main Street village is the heart of community activity in Gloucester. It's the primary location for large street festivals like the annual Gloucester Daffodil Festival, art walks, and concerts on the Historic Courthouse Circle.

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Nearby cities

Virginia Beach

Norfolk

Newport News

Hampton

Suffolk

Portsmouth

Chesapeake

Petersburg

Williamsburg

Richmond

Sandston

Mechanicsville

Yorktown

Smithfield

Highland Springs

Montrose

Exmore

Hopewell

Carrollton

Gloucester Point

Tappahannock

Windsor

Urbanna

Bellwood

East Highland Park

Waverly

Cape Charles

Colonial Heights

Chester

Fort Lee

Virginia Beach

Norfolk

Newport News

Hampton

Suffolk

Portsmouth

Chesapeake

Petersburg

Williamsburg

Richmond

Sandston

Mechanicsville

Yorktown

Smithfield

Highland Springs

Montrose

Exmore

Hopewell

Carrollton

Gloucester Point

Tappahannock

Windsor

Urbanna

Bellwood

East Highland Park

Waverly

Cape Charles

Colonial Heights

Chester

Fort Lee

Online Events

AI Animation Studio: Create Kids' Cartoons

HBR Book Webinar: Resilient Optimism

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(ONLINE) Women on the Move with Ann Patchett

Humanitarian Water Engineering Fall 2026

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