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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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Annual Oyster Roast @The Rose Family Farm primary image

Annual Oyster Roast @The Rose Family Farm

Today • 3:00 PM

6045 Everets Road, Suffolk VA 23434

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DIY Fused Glass Open Studio primary image

DIY Fused Glass Open Studio

Saturday • 11:00 AM

Happy Hour Glass Works

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

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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CE& H Ruritan Annual Oyster Roast primary image

CE& H Ruritan Annual Oyster Roast

Sat, Nov 14 • 1:00 PM

C.E.&H. Ruritan Club

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"The Shift: When Relationships Change" primary image

"The Shift: When Relationships Change"

Fri, Nov 20 • 7:00 PM

M& S Everyone Assistant

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Southside Ballet Studio presents The Nutcracker - 1 pm primary image

Southside Ballet Studio presents The Nutcracker - 1 pm

Sat, Dec 5 • 1:00 PM

Suffolk Center for Cultural Arts

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Pathways to Purpose Black Tie Gala primary image

Pathways to Purpose Black Tie Gala

Sat, Dec 5 • 5:00 PM

Hub 757

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Christmas Cookie Decorating Class @ Knotts Coffee Company primary image

Christmas Cookie Decorating Class @ Knotts Coffee Company

Thu, Dec 17 • 6:00 PM

Knotts Coffee Company

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Annual Oyster Roast @The Rose Family Farm primary image

Annual Oyster Roast @The Rose Family Farm

Today • 3:00 PM

6045 Everets Road, Suffolk VA 23434

Check ticket price on event

DIY Fused Glass Open Studio primary image

DIY Fused Glass Open Studio

Saturday • 11:00 AM

Happy Hour Glass Works

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

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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CE& H Ruritan Annual Oyster Roast primary image

CE& H Ruritan Annual Oyster Roast

Sat, Nov 14 • 1:00 PM

C.E.&H. Ruritan Club

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"The Shift: When Relationships Change" primary image

"The Shift: When Relationships Change"

Fri, Nov 20 • 7:00 PM

M& S Everyone Assistant

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Southside Ballet Studio presents The Nutcracker - 1 pm primary image

Southside Ballet Studio presents The Nutcracker - 1 pm

Sat, Dec 5 • 1:00 PM

Suffolk Center for Cultural Arts

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Pathways to Purpose Black Tie Gala primary image

Pathways to Purpose Black Tie Gala

Sat, Dec 5 • 5:00 PM

Hub 757

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Christmas Cookie Decorating Class @ Knotts Coffee Company primary image

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

26 miles away

Newport News

24 miles away

Chesapeake

26 miles away

Suffolk

13 miles away

Portsmouth

22 miles away

Petersburg

46 miles away

Williamsburg

32 miles away

Elizabeth City

46 miles away

Yorktown

32 miles away

Smithfield

13 miles away

Carrollton

15 miles away

Ettrick

47 miles away

Emporia

45 miles away

Franklin

14 miles away

Gloucester Point

33 miles away

Waverly

25 miles away

Colonial Heights

48 miles away

Surry

23 miles away

Poquoson

28 miles away

Charles City

41 miles away

Fort Lee

44 miles away

Gloucester Courthouse

42 miles away

Mathews

49 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

26 miles away

Newport News

24 miles away

Chesapeake

26 miles away

Suffolk

13 miles away

Portsmouth

22 miles away

Petersburg

46 miles away

Williamsburg

32 miles away

Elizabeth City

46 miles away

Yorktown

32 miles away

Smithfield

13 miles away

Carrollton

15 miles away

Ettrick

47 miles away

Emporia

45 miles away

Franklin

14 miles away

Gloucester Point

33 miles away

Waverly

25 miles away

Colonial Heights

48 miles away

Surry

23 miles away

Poquoson

28 miles away

Charles City

41 miles away

Fort Lee

44 miles away

Gloucester Courthouse

42 miles away

Mathews

49 miles away

Rich Square

48 miles away

Murfreesboro

32 miles away

Ahoskie

38 miles away

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Today • 12:00 PM PDT

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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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MENTORSHOP: Using Claude AI to Build a SaaS Site in about a Week primary image

MENTORSHOP: Using Claude AI to Build a SaaS Site in about a Week

Today • 12:00 PM PDT

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Turn Your Ideas Into Income

Today • 10:00 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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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 primary image

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 primary image

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 primary image

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

Sat, Dec 19 • 10:00 AM PST

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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.