Fall Festivals in Monroe County: Local Guide 2025
Looking for weekend ideas close to home? Fall in Monroe County is full of local flavor, from bustling farmers markets to family-friendly festivals. These events aren’t just fun—they’re a great way to explore our small towns, neighborhoods, meet local vendors, and feel more connected to the community.
Address: Columbia, IL
Dates / Time: Thursday, October 9, 2025, 4:00 PM – 9:00 PM
Short Description: A bewitching evening featuring themed shopping, food, drinks, and entertainment at participating businesses along Historic Main Street. Dress in your witchiest attire for a chance to win prizes.
Ticket Info: Free to attend; Very Important Witch (VIW) tickets available for early shopping and exclusive perks.
Parking: Street parking available along Main Street and nearby areas.
Pet Policy: Leashed pets allowed on public property; check with individual businesses for specific policies.
Accessibility: Sidewalks are accessible; some businesses may have limited interior accessibility.
Neighborhood & community insight:
This event brings the community together, showcasing the charm of Columbia's small businesses, both on and off Main Street.
Waterloo Sportsman's Club Haunted Trail & Hayride
Address: 4903 Sportsman Road, Waterloo, IL 62298
Dates / Time: October 3, 4, 10, 11, 17, 18, 2025, 7:00 PM – 11:00 PM
Short Description: Experience a thrilling haunted trail and hayride suitable for all ages. Enjoy food, drinks, and games for kids in a spooky setting.
Ticket Info: $20 per person; Pumpkin Express available for younger children.
Parking: On-site parking available; follow event signage.
Pet Policy: Not specified; contact organizers for clarification.
Accessibility: Trail may have uneven terrain; contact organizers for specific accessibility information.
Neighborhood & community insight:
The Haunted Trail offers a fun and spooky experience for families and thrill-seekers alike, supporting the local community through its long-standing tradition.
Columbia Scarecrow Crawl
Address: Historic Main Street, Columbia, IL 62236
Dates / Time: October 6 – October 31, 2025
Short Description: A month-long display of creatively decorated scarecrows by residents, schools, and businesses. Stroll down Main Street to enjoy the festive displays and vote for your favorites.
Ticket Info: Free to participate and view.
Parking: Street parking available along Main Street and nearby areas.
Pet Policy: Leashed pets allowed; be mindful of crowds and decorations.
Accessibility: Sidewalks are accessible; some displays may be on private property.
Neighborhood & community insight:
The Scarecrow Crawl fosters community spirit and allows residents to showcase their creativity, enhancing the festive atmosphere of Columbia's Main Street. Don't forget to vote for your favorite!
Address: Monroe County Courthouse Courtyard, 100 S Main St, Waterloo, IL 62298
Dates / Time: Saturday, October 11, 2025 — 9:00 AM to 4:00 PM
Short Description: A classic small-town fall festival with family fun, craft vendors, pumpkin displays, bake sales, kids’ activities, community booths.
Ticket Info: Free, but many opportunities to purchase items or concessions.
Parking: Street parking around downtown Waterloo, lots near the courthouse, overflow parking in adjacent neighborhoods.
Pet Policy: Pet-friendly (leashed).
Accessibility: Downtown area is relatively flat; sidewalk access and courthouse courtyard should have accessible routes. For wheelchair or stroller access, confirm with organizers.
Neighborhood & community insight:
PumpkinFest gives locals and visitors a chance to stroll downtown Waterloo, enjoy the historic district (like the area around the Monroe County Courthouse), and visit shops in the Waterloo neighborhoods that radiate from Main Street. It supports local artisans, nonprofits, and encourages people to explore the walkable core of Waterloo.
Address: Downtown Waterloo, IL 62298
Dates / Time: Thursday, October 16, 2025, 4:00 PM – 9:00 PM
Short Description: An evening of spooky fun with themed shopping, food, and entertainment at participating businesses in downtown Waterloo. Dress in your best witchy attire for a chance to win prizes.
Ticket Info: Free to attend; check with individual businesses for any special offers.
Parking: Street parking available throughout downtown Waterloo.
Pet Policy: Leashed pets allowed in public spaces; check with individual businesses for specific policies.
Accessibility: Sidewalks are accessible; some businesses may have limited interior accessibility.
Neighborhood & community insight:
This event highlights the vibrant downtown area of Waterloo, encouraging residents to explore local shops and eateries while celebrating the Halloween season.
Explore [City]
Which farmers' market or festival is your favorite? We'd love your feedback—or ask us for tips on the best neighborhoods to explore this fall.