Spirit of Ripley Festival Oct. 30; Chili Cook-Off Signups Open

The Spirit of Ripley Festival and Chili Cook-Off returns to the downtown Ripley square on Friday, Oct. 30, and Ripley Main Street Association is now signing up chili cooks, booth teams and trunk-or-treat participants. The community event runs from 5:30 to 9 p.m. around the historic square.

Organizers describe the night as a celebration featuring “local businesses, community organizations, food, activities and plenty of hometown spirit.” It lands the night before Halloween, giving families a safe, walkable place to trick-or-treat downtown.

Spirit of Ripley Festival at a Glance

• When: Friday, Oct. 30, 2026, 5:30 to 9 p.m.
• Where: The Square in downtown Ripley (111 E. Spring St. area)
• Hosted by: Ripley Main Street Association / Visit Ripley
• Highlights: Chili Cook-Off, decorated Spirit Booths, Trunk-or-Treat, food and family activities

How to Enter the Chili Cook-Off, Spirit Booths or Trunk-or-Treat

Registration is open online through Ripley Main Street’s sign-up page, which runs through Oct. 30. There are three ways to take part:

• Chili Cook-Off: Cooks enter to see whose chili is the best in town. Entry is $25, or $15 for Ripley Main Street members.
• Spirit Booth: Businesses, churches and groups can set up a decorated booth with festive giveaways. Booths are $25, or $15 for members.
• Trunk-or-Treat: Participants decorate a vehicle trunk and hand out treats. Registration is $15, or $5 for members.

A combined Chili Cook-Off and Spirit Booth registration is also available for $40. Member-priced spots and trunk-or-treat spaces are listed in limited numbers, so groups that want in should register early.

The sign-up page shows separate prices for Ripley Main Street members and non-members. Businesses and organizations thinking about joining the association can ask about membership when they call, since member pricing cuts entry costs for every option. Organizers had not posted judging details or prize information for the cook-off as of Wednesday.

Sign up at the Spirit of Ripley registration page. Questions can go to Ripley Main Street at (662) 512-0226.

A Busy Fall on the Ripley Square

The festival caps a full October downtown. Jefferson Street Tap Room is hosting Oktoberfest on the Ripley square Oct. 3, and Ripley Main Street recently announced that the Brown & Covington artisan marketplace is coming to South Commerce Street.

The Spirit of Ripley Festival has become a Halloween-season tradition for Tippah County families, bringing kids in costume, local cooks and community groups together on the square for one evening. Watch Visit Ripley and the Ripley Main Street Facebook page for any updates on vendors, judging or schedule changes as the date gets closer.

Source: Visit Ripley