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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Events near Gloucester

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Candlelight Dinner With Edgar Allan Poe

Friday • 6:00 PM

Shields Tavern

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Haunted Cellar

Friday • 6:00 PM

Williamsburg Winery, Ltd.

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Cheese Making Workshop

Thu, Nov 12 • 2:00 PM

Montague Kitchen & Cookery School

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Pumpkins, Petals, & Praise

Fri, Nov 20 • 6:00 PM

4291 Soles Ln

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Holiday Light Stroll 2026 presented by Langley Federal Credit Union

Tue, Nov 24 • 5:00 PM

Woodside High School - Bus Staging

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65th Annual Christmas Homes Tour in Colonial Williamsburg

Sat, Dec 5 • 9:00 AM

West Duke of Gloucester Street

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Chocolate Making Workshop

Sat, Dec 5 • 2:30 PM

Williamsburg Winery Wine Bar

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2027 William & Mary Law School Negotiation Tournament

Fri, Feb 26 • 8:30 AM

William & Mary Law School

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Candlelight Dinner With Edgar Allan Poe

Friday • 6:00 PM

Shields Tavern

Check ticket price on event

Haunted Cellar

Friday • 6:00 PM

Williamsburg Winery, Ltd.

Check ticket price on event

Cheese Making Workshop

Thu, Nov 12 • 2:00 PM

Montague Kitchen & Cookery School

Check ticket price on event

Pumpkins, Petals, & Praise

Fri, Nov 20 • 6:00 PM

4291 Soles Ln

Check ticket price on event

Holiday Light Stroll 2026 presented by Langley Federal Credit Union

Tue, Nov 24 • 5:00 PM

Woodside High School - Bus Staging

Check ticket price on event

65th Annual Christmas Homes Tour in Colonial Williamsburg

Sat, Dec 5 • 9:00 AM

West Duke of Gloucester Street

Check ticket price on event

Chocolate Making Workshop

Sat, Dec 5 • 2:30 PM

Williamsburg Winery Wine Bar

Check ticket price on event

2027 William & Mary Law School Negotiation Tournament

Fri, Feb 26 • 8:30 AM

William & Mary Law School

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Exmore

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Montross

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Gloucester Point

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Tappahannock

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Windsor

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Poquoson

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Waverly

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Colonial Heights

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Virginia Beach

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Norfolk

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Hampton

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Newport News

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Chesapeake

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Suffolk

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Portsmouth

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Williamsburg

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Petersburg

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Richmond

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Sandston

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Montrose

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Yorktown

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Smithfield

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Highland Springs

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Mechanicsville

48 miles away

Cape Charles

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Carrollton

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East Highland Park

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Urbanna

16 miles away

Exmore

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Montross

50 miles away

Gloucester Point

11 miles away

Tappahannock

40 miles away

Windsor

43 miles away

Poquoson

21 miles away

Surry

25 miles away

Warsaw

40 miles away

Waverly

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Colonial Heights

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Online Events

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ATL’S BIGGEST HALLOWEEN TAKEOVER

Friday • 10:00 PM EDT

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Understanding ADHD-Fostercarers: Connection, Regulation & Support

Wed, Nov 4 • 10:00 AM 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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The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

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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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But That’s What They Said! Conceptual Accuracy Beyond the Words

Sat, Dec 19 • 10:00 AM PST

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ATL’S BIGGEST HALLOWEEN TAKEOVER

Friday • 10:00 PM EDT

Check ticket price on event

Understanding ADHD-Fostercarers: Connection, Regulation & Support

Wed, Nov 4 • 10:00 AM 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

The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

Check ticket price on event

The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

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

But That’s What They Said! Conceptual Accuracy Beyond the Words

Sat, Dec 19 • 10:00 AM PST

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.

Events near Gloucester

Candlelight Dinner With Edgar Allan Poe

Haunted Cellar

Cheese Making Workshop

Pumpkins, Petals, & Praise

Holiday Light Stroll 2026 presented by Langley Federal Credit Union

65th Annual Christmas Homes Tour in Colonial Williamsburg

Chocolate Making Workshop

2027 William & Mary Law School Negotiation Tournament

Candlelight Dinner With Edgar Allan Poe

Haunted Cellar

Cheese Making Workshop

Pumpkins, Petals, & Praise

Holiday Light Stroll 2026 presented by Langley Federal Credit Union

65th Annual Christmas Homes Tour in Colonial Williamsburg

Chocolate Making Workshop

2027 William & Mary Law School Negotiation Tournament

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Nearby cities

Virginia Beach

Norfolk

Hampton

Newport News

Chesapeake

Suffolk

Portsmouth

Williamsburg

Petersburg

Richmond

Sandston

Montrose

Yorktown

Smithfield

Highland Springs

Mechanicsville

Cape Charles

Carrollton

East Highland Park

Urbanna

Exmore

Montross

Gloucester Point

Tappahannock

Windsor

Poquoson

Surry

Warsaw

Waverly

Colonial Heights

Virginia Beach

Norfolk

Hampton

Newport News

Chesapeake

Suffolk

Portsmouth

Williamsburg

Petersburg

Richmond

Sandston

Montrose

Yorktown

Smithfield

Highland Springs

Mechanicsville

Cape Charles

Carrollton

East Highland Park

Urbanna