Best events in
Gloucester Point

As life along the York River shifts with the seasons, there are many events and things to do in Gloucester Point, VA. Community life often centers on the historic Main Street in Gloucester Courthouse, while the Yorktown riverfront hosts larger outdoor gatherings. This mix of small-town charm and waterfront activity defines the local scene.

An afternoon on Gloucester's Main Street might start at the Gloucester Brewing Company, which hosts regular trivia, music bingo, and open mic nights.
The regional music scene includes everything from bluegrass at Flat Iron Crossroads to the Virginia Symphony's annual, free Symphony Under the Stars concert.
Yorktown's Riverwalk Landing is a hub for outdoor events, hosting the weekly Yorktown Market Days and the Sounds of Summer Concert Series.

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Events near Gloucester Point

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Cheese Making Workshop

Sun, Nov 8 • 3:00 PM

Frothy Moon Brewhouse

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Chef's Notebook

Wed, Nov 11 • 6:00 PM

Williamsburg Winery, Ltd.

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4th Annual Adult Prom Night

Thu, Nov 12 • 5:00 PM

Kiln Creek Golf Club and Resort

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Jazz Legacy Gala 2026: Festival Friday

Fri, Nov 13 • 5:30 PM

Hampton Roads Convention Center

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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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Women's Council of REALTORS Virginia 2027 Leadership Team Installation

Fri, Dec 18 • 6:00 PM

The Fort Eustis Club

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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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Cheese Making Workshop

Sun, Nov 8 • 3:00 PM

Frothy Moon Brewhouse

Check ticket price on event

Chef's Notebook

Wed, Nov 11 • 6:00 PM

Williamsburg Winery, Ltd.

Check ticket price on event

4th Annual Adult Prom Night

Thu, Nov 12 • 5:00 PM

Kiln Creek Golf Club and Resort

Check ticket price on event

Jazz Legacy Gala 2026: Festival Friday

Fri, Nov 13 • 5:30 PM

Hampton Roads Convention Center

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

Women's Council of REALTORS Virginia 2027 Leadership Team Installation

Fri, Dec 18 • 6:00 PM

The Fort Eustis Club

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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Gloucester Courthouse

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Virginia Beach

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Norfolk

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Chesapeake

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Newport News

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Suffolk

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Portsmouth

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Carrollton

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Montrose

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Windsor

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Urbanna

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Exmore

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Highland Springs

49 miles away

Franklin

47 miles away

Waverly

36 miles away

Colonial Heights

49 miles away

Chester

50 miles away

Tappahannock

50 miles away

Poquoson

11 miles away

Hopewell

43 miles away

Charles City

32 miles away

Central Garage

49 miles away

Fort Lee

45 miles away

Gloucester Courthouse

9 miles away

Online Events

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Gunpowder Plot - punishing the plotters

Wednesday • 7:30 PM GMT

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

Thursday • 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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Physicians Financial Wellness Conference 2026

Sat, Nov 14 • 1:00 PM EST

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Debt-A-Thon 2026

Fri, Nov 27 • 9:00 AM PST

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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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Gunpowder Plot - punishing the plotters

Wednesday • 7:30 PM GMT

Check ticket price on event

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

Thursday • 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

Physicians Financial Wellness Conference 2026

Sat, Nov 14 • 1:00 PM EST

Check ticket price on event

Debt-A-Thon 2026

Fri, Nov 27 • 9:00 AM PST

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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Points of Interest near Gloucester Point

Tyndalls Point Park

Frequently asked questions about Gloucester Point

What are some family-friendly events in the Gloucester Point area?

The region offers many daytime, family-friendly events, especially on weekends. Yorktown Market Days provides a lively atmosphere with food and music, while the annual Daffodil Festival is a beloved community tradition. Gloucester Point Beach Park is another great spot for casual outdoor recreation.

Where can I find live music events near Gloucester Point?

Flat Iron Crossroads is a key venue for bluegrass and American roots music. For a more casual setting, Gloucester Brewing Company on Main Street has a regular schedule of live music and open mic nights. Yorktown's waterfront also hosts free concerts.

Are there any recurring comedy shows?

Mobjack Tavern in Hayes periodically hosts a popular comedy night. The event brings nationally touring comedians to the area for an evening show. Check local schedules for dates and performers for this recurring event.

How can I discover free events to attend?

Many community events in the area are free to the public. Yorktown's Sounds of Summer Concert Series and the annual Symphony Under the Stars are two popular free music events. The Virginia Institute of Marine Science also offers a monthly public lecture series.

What is the local food and drink scene like?

The scene is centered on casual, community-oriented spots rather than fine dining. Gloucester Brewing Company serves as a local hub with its craft beer and weekly events. For a larger tasting event, the annual Gloucester Wine Festival gathers local wineries and vendors.

Is there much nightlife in Gloucester Point?

The nightlife here is low-key and ends relatively early. Instead of clubs, evenings revolve around pub-style events at places like Gloucester Brewing Company. Mobjack Tavern also offers evening entertainment with its periodic comedy nights.

What's a good date night idea in the area?

A great date night could involve seeing a live show or enjoying a local brew. Catching a bluegrass performance at Flat Iron Crossroads offers a unique experience. Alternatively, a casual evening at Gloucester Brewing Company for trivia or music is a popular local choice.

What kind of outdoor events happen in Yorktown?

Yorktown's waterfront is the primary location for large outdoor events. Riverwalk Landing is home to the weekly Yorktown Market Days, which runs from spring through fall. The area also hosts the free Sounds of Summer Concert Series, drawing crowds to the riverfront.

Events near Gloucester Point

Cheese Making Workshop

Chef's Notebook

4th Annual Adult Prom Night

Jazz Legacy Gala 2026: Festival Friday

Holiday Light Stroll 2026 presented by Langley Federal Credit Union

65th Annual Christmas Homes Tour in Colonial Williamsburg

Women's Council of REALTORS Virginia 2027 Leadership Team Installation

2027 William & Mary Law School Negotiation Tournament

Cheese Making Workshop

Chef's Notebook

4th Annual Adult Prom Night

Jazz Legacy Gala 2026: Festival Friday

Holiday Light Stroll 2026 presented by Langley Federal Credit Union

65th Annual Christmas Homes Tour in Colonial Williamsburg

Women's Council of REALTORS Virginia 2027 Leadership Team Installation

2027 William & Mary Law School Negotiation Tournament

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Nearby cities

Virginia Beach

Norfolk

Hampton

Chesapeake

Newport News

Suffolk

Portsmouth

Petersburg

Williamsburg

Smithfield

Yorktown

Sandston

Cape Charles

Carrollton

Montrose

Windsor

Urbanna

Exmore

Highland Springs

Franklin

Waverly

Colonial Heights

Chester

Tappahannock

Poquoson

Hopewell

Charles City

Central Garage

Fort Lee

Gloucester Courthouse

Virginia Beach

Norfolk

Hampton

Chesapeake

Newport News

Suffolk

Portsmouth

Petersburg

Williamsburg

Smithfield

Yorktown

Sandston

Cape Charles

Carrollton

Montrose

Windsor

Urbanna

Exmore

Highland Springs