Best events in
Winfield

Centered on historic Main Streets and seasonal celebrations, the area offers a variety of events and things to do in Winfield, MD. Community life often unfolds in the downtown hubs of nearby Sykesville and Westminster, which host a range of cultural gatherings. From outdoor festivals at the Carroll County Farm Museum to performances at the Carroll Arts Center, the local character shines through its happenings.

Explore Sykesville’s historic Main Street, home to the weekly Sykesville Farmers' Market and annual street festivals like the Sippin' on Summer Festival.
Find gallery exhibits, films, and live theater at the Carroll Arts Center in downtown Westminster, a central hub for regional arts and culture.
Join in on community traditions at venues like the Winfield Volunteer Fire Department Hall, known for flea markets and food truck nights.

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Online Group Reading Nov 1 | Psychic Medium Michelle Russell

Today • 8:00 PM AST

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

Thursday • 1:00 PM GMT

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The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

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REVISED Cottage Food Safety Statewide Online Training

Fri, Nov 13 • 9:00 AM MST

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Corn as a partner and gift giver: Voices of respect

Wed, Nov 18 • 10:00 AM CST

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Virtual - Powerful Gottman Method Couples Therapy Tools

Fri, Nov 20 • 8:00 AM CST

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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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Online Group Reading Nov 1 | Psychic Medium Michelle Russell

Today • 8:00 PM AST

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

The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

Check ticket price on event

REVISED Cottage Food Safety Statewide Online Training

Fri, Nov 13 • 9:00 AM MST

Check ticket price on event

Corn as a partner and gift giver: Voices of respect

Wed, Nov 18 • 10:00 AM CST

Check ticket price on event

Virtual - Powerful Gottman Method Couples Therapy Tools

Fri, Nov 20 • 8:00 AM CST

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

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Events near Winfield

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2026 Women Who Soar Conference (Baltimore)

Thursday • 5:00 PM

Set the Captives Free Outreach Center

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SECRET GARDEN FUNK, SOUL, and TRAILRIDE MUSIC, ARTS and WINE FESTIVAL

Sat, Nov 7 • 11:00 AM

Carroll County Farm Museum

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Rooted in Wellness- Fire Cider Workshop

Sat, Nov 7 • 10:00 AM

3302 Mail Rd

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Lamkin3 Entertainment Presents: The Return of Terri Green

Sun, Nov 8 • 7:00 PM

The Collective - Encore

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GIEI: Winter Sowing

Sat, Nov 14 • 10:00 AM

Carroll County Public Library - Finksburg Branch

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Kindness Kits- Baltimore Chapter

Sat, Nov 21 • 12:30 PM

1301 Reisterstown Rd

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1/6/27 Small Group Mediumship Experience w/ Medium Debbie

Wed, Jan 6 • 6:30 PM

O'Lordan's Irish Pub

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Charm City Romanticon 2027

Fri, Apr 2 • 2:00 PM

Turf Valley Resort

Check ticket price on event

2026 Women Who Soar Conference (Baltimore)

Thursday • 5:00 PM

Set the Captives Free Outreach Center

Check ticket price on event

SECRET GARDEN FUNK, SOUL, and TRAILRIDE MUSIC, ARTS and WINE FESTIVAL

Sat, Nov 7 • 11:00 AM

Carroll County Farm Museum

Check ticket price on event

Rooted in Wellness- Fire Cider Workshop

Sat, Nov 7 • 10:00 AM

3302 Mail Rd

Check ticket price on event

Lamkin3 Entertainment Presents: The Return of Terri Green

Sun, Nov 8 • 7:00 PM

The Collective - Encore

Check ticket price on event

GIEI: Winter Sowing

Sat, Nov 14 • 10:00 AM

Carroll County Public Library - Finksburg Branch

Check ticket price on event

Kindness Kits- Baltimore Chapter

Sat, Nov 21 • 12:30 PM

1301 Reisterstown Rd

Check ticket price on event

1/6/27 Small Group Mediumship Experience w/ Medium Debbie

Wed, Jan 6 • 6:30 PM

O'Lordan's Irish Pub

Check ticket price on event

Charm City Romanticon 2027

Fri, Apr 2 • 2:00 PM

Turf Valley Resort

Check ticket price on event

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Nearby cities

Washington

37 miles away

Baltimore

26 miles away

Arlington

39 miles away

Alexandria

44 miles away

Columbia

20 miles away

Silver Spring

31 miles away

College Park

32 miles away

Hagerstown

38 miles away

Fairfax

43 miles away

Towson

24 miles away

Bethesda

32 miles away

Reston

38 miles away

Tysons Corner

38 miles away

Annapolis

44 miles away

Gaithersburg

23 miles away

Rockville

25 miles away

North Bethesda

28 miles away

Crownsville

42 miles away

Frederick

19 miles away

Glen Burnie

32 miles away

Bowie

37 miles away

Bel Air South

40 miles away

National Harbor

46 miles away

Vienna

40 miles away

McLean

37 miles away

Spring Ridge

19 miles away

Leesburg

35 miles away

Konterra

28 miles away

Catonsville

21 miles away

Chantilly

44 miles away

Washington

37 miles away

Baltimore

26 miles away

Arlington

39 miles away

Alexandria

44 miles away

Columbia

20 miles away

Silver Spring

31 miles away

College Park

32 miles away

Hagerstown

38 miles away

Fairfax

43 miles away

Towson

24 miles away

Bethesda

32 miles away

Reston

38 miles away

Tysons Corner

38 miles away

Annapolis

44 miles away

Gaithersburg

23 miles away

Rockville

25 miles away

North Bethesda

28 miles away

Crownsville

42 miles away

Frederick

19 miles away

Glen Burnie

32 miles away

Bowie

37 miles away

Bel Air South

40 miles away

National Harbor

46 miles away

Vienna

40 miles away

McLean

37 miles away

Spring Ridge

19 miles away

Leesburg

35 miles away

Konterra

28 miles away

Catonsville

21 miles away

Chantilly

44 miles away

Frequently asked questions about Winfield

What are some family-friendly things to do near Winfield?

Look for seasonal festivals and community markets in the area's towns. The Carroll County Farm Museum hosts large outdoor events, and the weekly Sykesville Farmers' Market often includes activities suitable for all ages. Many local gatherings have a family-friendly atmosphere.

Where can I find food and drink events in the Winfield area?

The historic main streets of Sykesville and Mount Airy are hubs for food-focused events. Mount Airy hosts weekly food truck nights, while Sykesville's annual Sippin' on Summer Festival celebrates local beverages. The Maryland Wine Festival is also a major annual draw.

Are there venues for art events and performances around Winfield?

The Carroll Arts Center in Westminster is the primary destination for arts and culture. The downtown theater presents a regular schedule of gallery exhibits, film screenings, and live performances, making it a cultural anchor for the entire region.

What kind of outdoor events happen in the region?

Outdoor events are common, especially farmers' markets and large-scale festivals. The Carroll County Agriculture Center and Carroll County Farm Museum provide ample space for annual fairs and festivals. Towns like Sykesville also close their main streets for seasonal celebrations.

How can I find date night ideas or nightlife events?

Date night activities often revolve around dinner and a show in Westminster or Sykesville. The Carroll Arts Center offers evening films and performances, while pubs and restaurants in downtown Westminster sometimes feature live music.

Which local events are typically free to enter?

Many community gatherings like farmers' markets are free to attend. The weekly Mount Airy Farmers' Market and Sykesville Farmers' Market offer a chance to browse local goods and enjoy the atmosphere, though vendors charge for products.

Where's a good place to see live music?

The Carroll Arts Center in Westminster is a key venue for ticketed musical performances. For more casual settings, some pubs and restaurants in the downtown areas of Westminster and Mount Airy occasionally host live local musicians.

What's the event scene like on Sykesville's Main Street?

Sykesville's Main Street is a lively hub for community events. It hosts a popular weekly farmers' market from spring to fall and is known for its annual street festivals that draw visitors from around the region to its historic downtown.