Best events in
Winchester

Events and things to do in Winchester, KS are deeply rooted in the community life of Jefferson County. The local scene is characterized by long-standing traditions, a focus on regional history, and plenty of outdoor recreation. Much of the activity is centered in nearby towns like Oskaloosa and Perry, which host the area's main festivals and gatherings.

Experience the heart of community life in Oskaloosa, where the historic courthouse square and Old Jefferson Town host markets and family-friendly programs.
Enjoy outdoor recreation and community gatherings centered around the activities at Perry State Park and Perry Lake.
Celebrate local traditions at annual events like the Jefferson County Fair in Valley Falls or the Perry Fall Festival.

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Roeland Park

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Events near Winchester

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Hearth Fires Festival - 2026

Thu, Oct 15 • 4:00 PM

Gaea Retreat Center

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Collage Art Earrings Party

Sat, Oct 17 • 1:00 PM

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A Beginner's Guide to Treating OCD

Fri, Oct 23 • 11:00 AM

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Weston Whiskey Fest

Sat, Oct 24 • 2:00 PM

Weston Burley House Inc

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LAAND Presents: Squirrel Flower at The White Schoolhouse!

Sat, Oct 24 • 7:30 PM

White Schoolhouse

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Watkins Museum After Dark

Fri, Oct 30 • 7:00 PM

Watkins Museum of History

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The Pelican Crèche 2026

Sat, Nov 7 • 8:00 AM

819 Commercial St

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Magnolia and Mistletoe Bridal Brunch and Experience

Sat, Dec 5 • 10:00 AM

Deer Ridge Estate

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Hearth Fires Festival - 2026

Thu, Oct 15 • 4:00 PM

Gaea Retreat Center

Check ticket price on event

Collage Art Earrings Party

Sat, Oct 17 • 1:00 PM

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Check ticket price on event

A Beginner's Guide to Treating OCD

Fri, Oct 23 • 11:00 AM

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Weston Whiskey Fest

Sat, Oct 24 • 2:00 PM

Weston Burley House Inc

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LAAND Presents: Squirrel Flower at The White Schoolhouse!

Sat, Oct 24 • 7:30 PM

White Schoolhouse

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Watkins Museum After Dark

Fri, Oct 30 • 7:00 PM

Watkins Museum of History

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The Pelican Crèche 2026

Sat, Nov 7 • 8:00 AM

819 Commercial St

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Frequently asked questions about Winchester

What are some family-friendly events in the Winchester area?

The Winchester area offers many family-friendly events, especially in Oskaloosa. Old Jefferson Town hosts historical programs, while the annual Jefferson County Fair features livestock shows and classic fair fun. The Oskaloosa Old Settlers Reunion is another popular multi-day tradition for all ages.

Where can I find live music events near Winchester?

Live music is a key part of local festivals and seasonal programs. The Oskaloosa Summer Concert Series features the city band on its historic bandstand. You can also find live performances as part of the annual Jefferson County Fair and Oskaloosa Old Settlers Reunion.

Are there free things to do in the Winchester area?

Yes, enjoying the outdoors is a popular free activity in the region. Perry State Park and Perry Lake offer trails and scenic views. Attending a performance during the Oskaloosa Summer Concert Series is another great free event for the community.

How does the local scene handle nightlife?

The nightlife scene around Winchester is very quiet and community-focused. Local events tend to be earlier in the evening, such as the summer concert series. For a wider selection of late-night bars and entertainment, residents typically drive to Lawrence or Topeka.

What kind of outdoor events are popular near Winchester?

Outdoor events revolve around Perry Lake and the surrounding state park. Activities include boating, hiking, and attending gatherings within Perry State Park. The annual Perry Fall Festival also brings the community together outdoors with craft vendors and a car show.

Can I find food events or farmers markets in the area?

The Perry Lecompton Farmers Market is a great spot for local goods and operates seasonally. Additionally, annual gatherings like the Perry Fall Festival and Oskaloosa Old Settlers Reunion feature numerous food vendors as part of the festivities.

Is Oskaloosa a good place to find community gatherings?

Oskaloosa is the primary hub for community events in the county. Its historic square is the site of seasonal markets and festivals. Old Jefferson Town also hosts many programs, and the annual Oskaloosa Old Settlers Reunion is a major multi-day gathering for the community.

Which major annual festivals happen near Winchester?

The region's calendar is marked by several key annual festivals. The Jefferson County Fair is a major summer event in Valley Falls. Other highlights include the Perry Fall Festival and the Oskaloosa Old Settlers Reunion, both of which are long-standing community traditions.

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Nearby cities

Kansas City

Overland Park

Olathe

Topeka

Lawrence

Kansas City

Independence

Lenexa

St. Joseph

Liberty

Shawnee

Mission Woods

Leavenworth

Prairie Village

Parkville

Kearney

Spring Hill

Riverside

Gladstone

Hiawatha

Lansing

Atchison

Fairway

Tonganoxie

Bonner Springs

Ottawa

Merriam

Mission

Roeland Park

Gardner

Kansas City

Overland Park

Olathe

Topeka

Lawrence

Kansas City

Independence

Lenexa

St. Joseph

Liberty

Shawnee

Mission Woods

Leavenworth

Prairie Village

Parkville

Kearney

Spring Hill

Riverside

Gladstone

Hiawatha

Lansing

Atchison

Fairway

Tonganoxie

Bonner Springs

Ottawa

Merriam

Mission

Roeland Park

Gardner

Online Events

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Today's RDH Virtual Dental Continuing Education (CE) Event - Oct. 17, 2026

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Lean Global Connection 2026

Washington Crossing the Delaware / The Crossing - Film History Livestream

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Washington Crossing the Delaware / The Crossing - Film History Livestream