Best events in
Windsor

Low-key weeknights transition into bustling weekend outings filled with local events and things to do across Windsor, VA. The Courthouse Highway corridor anchors the civic core with community facilities and casual roadside gathering spots. Nearby historic districts and parks expand the regional footprint for daytime exploration.

Along the Courthouse Highway corridor, visitors find Windsor Town Center hosting various community programs and gymnasium gatherings.
Redd's Filling Station offers a casual outdoor setting equipped with lawn games, mini-golf, and a relaxed patio bar.
Heritage Park provides open-air green space for public recreation directly alongside regional thoroughfares.

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Events near Windsor

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Pumpkin Time! DIY Fused Glass Open Studio

Thursday • 6:00 PM

Happy Hour Glass Works

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Suffolk Peanut Fest

Thursday • 4:00 PM

Festival Grounds

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GeoVirginia 2026 (Conference, Outings, & Sunday Social Registration Page)

Sun, Oct 18 • 11:00 AM

Smithfield Center

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Annual Oyster Roast @The Rose Family Farm

Wed, Oct 28 • 3:00 PM

6045 Everets Road, Suffolk VA 23434

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Women Celebrating Women: It's Who We Are, It's What We Do!

Sat, Oct 31 • 4:00 PM

138 S 6th St

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Firk Around & Find Out - A Cask Ale Festival at Nansemond Brewing Station

Sat, Nov 7 • 12:00 PM

Nansemond Brewing Station

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Southside Ballet Studio presents The Nutcracker - 1 pm

Sat, Dec 5 • 1:00 PM

Suffolk Center for Cultural Arts

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Christmas Cookie Decorating Class @ Knotts Coffee Company

Thu, Dec 17 • 6:00 PM

Knotts Coffee Company

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Pumpkin Time! DIY Fused Glass Open Studio

Thursday • 6:00 PM

Happy Hour Glass Works

Check ticket price on event

Suffolk Peanut Fest

Thursday • 4:00 PM

Festival Grounds

Check ticket price on event

GeoVirginia 2026 (Conference, Outings, & Sunday Social Registration Page)

Sun, Oct 18 • 11:00 AM

Smithfield Center

Check ticket price on event

Annual Oyster Roast @The Rose Family Farm

Wed, Oct 28 • 3:00 PM

6045 Everets Road, Suffolk VA 23434

Check ticket price on event

Women Celebrating Women: It's Who We Are, It's What We Do!

Sat, Oct 31 • 4:00 PM

138 S 6th St

Check ticket price on event

Firk Around & Find Out - A Cask Ale Festival at Nansemond Brewing Station

Sat, Nov 7 • 12:00 PM

Nansemond Brewing Station

Check ticket price on event

Southside Ballet Studio presents The Nutcracker - 1 pm

Sat, Dec 5 • 1:00 PM

Suffolk Center for Cultural Arts

Check ticket price on event

Christmas Cookie Decorating Class @ Knotts Coffee Company

Thu, Dec 17 • 6:00 PM

Knotts Coffee Company

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Nearby cities

Virginia Beach

36 miles away

Norfolk

26 miles away

Hampton

27 miles away

Newport News

24 miles away

Chesapeake

27 miles away

Suffolk

13 miles away

Portsmouth

22 miles away

Petersburg

46 miles away

Williamsburg

32 miles away

Elizabeth City

45 miles away

Yorktown

32 miles away

Smithfield

13 miles away

Ettrick

48 miles away

Emporia

45 miles away

Hopewell

46 miles away

Carrollton

15 miles away

Gloucester Point

33 miles away

Franklin

14 miles away

Colonial Heights

48 miles away

Waverly

25 miles away

Fort Lee

44 miles away

Jarratt

40 miles away

Poquoson

28 miles away

Rich Square

48 miles away

Murfreesboro

32 miles away

Ahoskie

38 miles away

Virginia Beach

36 miles away

Norfolk

26 miles away

Hampton

27 miles away

Newport News

24 miles away

Chesapeake

27 miles away

Suffolk

13 miles away

Portsmouth

22 miles away

Petersburg

46 miles away

Williamsburg

32 miles away

Elizabeth City

45 miles away

Yorktown

32 miles away

Smithfield

13 miles away

Ettrick

48 miles away

Emporia

45 miles away

Hopewell

46 miles away

Carrollton

15 miles away

Gloucester Point

33 miles away

Franklin

14 miles away

Colonial Heights

48 miles away

Waverly

25 miles away

Fort Lee

44 miles away

Jarratt

40 miles away

Poquoson

28 miles away

Rich Square

48 miles away

Murfreesboro

32 miles away

Ahoskie

38 miles away

Online Events

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

Today • 7:30 PM GMT+1

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AI Animation Studio: Create Kids' Cartoons

Thursday • 6:00 PM EDT

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HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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Humanitarian Water Engineering Fall 2026

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

Today • 7:30 PM GMT+1

Check ticket price on event

AI Animation Studio: Create Kids' Cartoons

Thursday • 6:00 PM EDT

Check ticket price on event

HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

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

Humanitarian Water Engineering Fall 2026

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 Windsor

Where are the best family-friendly events in Windsor, VA held?

Windsor Town Center serves as a primary hub for family-friendly events throughout the year. The facility provides large gymnasium spaces and youth rooms designed for community gatherings, seasonal programs, and public meetings.

What outdoor events happen near Courthouse Highway?

Heritage Park hosts community-focused outdoor events leveraging expansive green spaces along Courthouse Highway. The county facility supplies open recreational grounds suitable for public relaxation, casual strolls, and afternoon meetups throughout changing seasonal cycles and various regional gatherings.

Are there food and drink events in the historic district?

Redd's Filling Station delivers casual food and drink events centered around a historic gas station setting. Visitors enjoy a casual outdoor area equipped with lawn games, mini-golf, and a relaxed open-air bar paired with classic neighborhood fare.

How do the Monthly Pickers Markets operate?

The Monthly Pickers Markets operate on the monthly of each month through late autumn in the nearby historic district. These popular gatherings bring vintage vendors, local goods, and antique collectors together for daytime browsing and community commerce.

Which spots highlight local art events and artisan goods?

The Windsor Virginia Farmers Market highlights local art events by operating Sundays from mid-spring through early autumn. Stalls feature farm-fresh produce, regional plants, and handmade artisan goods supplied by dedicated area creators across the broader rural community.

Can visitors find seasonal vintage markets in the area?

Seasonal Vintage Markets occur annually in both spring and autumn, showcasing antique goods and regional crafts. These expansive community markets feature numerous food trucks and specialty vendors occupying local outdoor spaces throughout the wider historic district during daytime hours.

What activities define the downtown Windsor corridor?

The Downtown Windsor corridor defines local culture through civic facilities, community event spaces, and casual roadside spots. Visitors frequently explore nearby historic Smithfield for riverside green spaces like Windsor Castle Park, local pubs, and charming boutique shopping destinations.

Where can people enjoy date night ideas or casual outings?

Redd's Filling Station provides ideal date night ideas with its historic gas station vibe and outdoor bar. Couples can enjoy relaxed lawn games and mini-golf in an informal setting paired with casual evening dining experiences.

Events near Windsor

Pumpkin Time! DIY Fused Glass Open Studio

Suffolk Peanut Fest

GeoVirginia 2026 (Conference, Outings, & Sunday Social Registration Page)

Annual Oyster Roast @The Rose Family Farm

Women Celebrating Women: It's Who We Are, It's What We Do!

Firk Around & Find Out - A Cask Ale Festival at Nansemond Brewing Station

Southside Ballet Studio presents The Nutcracker - 1 pm

Christmas Cookie Decorating Class @ Knotts Coffee Company

Pumpkin Time! DIY Fused Glass Open Studio

Suffolk Peanut Fest

GeoVirginia 2026 (Conference, Outings, & Sunday Social Registration Page)

Annual Oyster Roast @The Rose Family Farm

Women Celebrating Women: It's Who We Are, It's What We Do!

Firk Around & Find Out - A Cask Ale Festival at Nansemond Brewing Station

Southside Ballet Studio presents The Nutcracker - 1 pm

Christmas Cookie Decorating Class @ Knotts Coffee Company

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Nearby cities

Virginia Beach

Norfolk

Hampton

Newport News

Chesapeake

Suffolk

Portsmouth

Petersburg

Williamsburg

Elizabeth City

Yorktown

Smithfield

Ettrick

Emporia

Hopewell

Carrollton

Gloucester Point

Franklin

Colonial Heights

Waverly

Fort Lee

Jarratt

Poquoson

Rich Square

Murfreesboro

Ahoskie

Virginia Beach

Norfolk

Hampton

Newport News

Chesapeake

Suffolk

Portsmouth

Petersburg

Williamsburg

Elizabeth City

Yorktown

Smithfield

Ettrick

Emporia

Hopewell

Carrollton

Gloucester Point

Franklin

Colonial Heights

Waverly

Fort Lee

Jarratt

Poquoson