Greenfield Indiana is packed with fall fun, local events, and seasonal charm, especially historic downtown Greenfield.
2025 GREENFIELD INDIANA FALL EVENTS
September Market on Main (Sept. 18) – Come support local businesses on the Courthouse Square and enjoy an evening of creativity, community, and fun at Market on Main!
2025 Greenfield Historic Home Tour – (Sept. 21) This year’s tour will include two downtown commercial buildings, the James Whitcomb Riley Boyhood Home, and 4 private residences.
Greenfield Farmers Market at the Fairgrounds – Through October, the farmers market is open every Saturday from 8am-Noon. Starting in November, it is only on the first and third Saturday from 10am-1pm. Up to 20 vendors participate in this farmers market.
Chalkfest in the Living Alley (Sept. 27) – Brought to you by Hancock County Arts.
Annual Rotary Steak N Bake Event (Sept. 27) –Don’t miss this annual night of food, fun, and giving back, put on by the Greenfield Rotary at the Hancock County Fairgrounds. Ticketed event.
9th Annual Hancock4Kids Superhero 5K, Kids’ Dash & Hero Dash (Sept. 20) – Begins at Hancock County Courthouse Plaza & Pennsy Trail. Come for the run, stay for the fun! Learn more on the event Facebook page.
Riley Festival (Oct. 2–5, 2025) – A four-day celebration honoring poet James Whitcomb Riley with parades, live entertainment, themed activities, and over 460 craft and food vendors.
Riley Park Turns 100! (Oct. 4, 2025) An afternoon of fun, history, and community brought to you by Greenfield Parks & Recreation. Enjoy 100 giveaways, a Ferris wheel, and plenty of ways to celebrate a century of memories in Greenfield’s beloved park.
Festival of Jack‑o‑Lanterns (Oct 25th -31st) Held annually at the James Whitcomb Riley Boyhood Home, this community pumpkin-carving display lights up the evenings, complete with voting and prizes for both child and adult artists. Keep an eye on their Facebook page for dates.
Hancock Health Foundation Annual Women Helping Women Celebration (Oct. 24) – This year’s theme is Hopelessly Devoted to Women’s Health. The annual fundraising event raises crucial funding for the Women’s Clinic, ensuring healthcare access for hundreds of local women in need.
Greenfield Main Street’s Boos & Brews (Adults‑Only, Oct. 25) – Downtown Greenfield transforms with an festive evening of food and drinks, a scavenger hunt, live music, artisan vendors, costume contests, and T‑shirt printing.
October Family-Fun Events
Art events all season long at Hancock County Creations Art Studio.
- Greenfield Parks Trunk or Treat at the Fairgrounds (Oct. 23)
- Tricks on Main in downtown Greenfield, ending with a free movie (Oct. 24)
- Arc of Hancock County & Remarkable Ranch Trunk or Treat (Oct. 26)
- Hank’s Spooktacular in the Hancock Regional Hospital Parking Garage (Oct. 30)
November Event Highlights
Greenfield Main Street Bags, Bourbon & Bingo Night (Nov. 15) – Ticketed fundraising event. Enjoy an exciting evening full of fun, fabulous designer bags, bourbon, raffle baskets, purse pull, 50/50, pull tabs and of course… BINGO!
Shop Small Saturday (Nov. 29) – Support your local merchants by shopping LOCAL on Shop Small Saturday, which is right after Thanksgiving each year. Be sure to pick up your Holiday Shopping Passport and enter to win gift certificates from downtown Greenfield merchants!
Local Fall Activities & Attractions
Tuttle Orchards
Just outside Greenfield, this local favorite offers apple picking, seasonal treats, pumpkin patches, hayrides, corn mazes, a farm store, play area, and a “cut your own flowers.” Don’t miss the delish donuts, cider slushies, and famous caramel apples!
This 73-acre farm for enough fun to fill an entire week! Grab your family’s pumpkins and enjoy a variety of activities, including a corn maze, gem mining, rock wall climb, duck races, hay mountain, hayrides, pedal karts, horseshoes, a ninja course and tons more. Go ahead and tag your Christmas tree beginning in September so it’s ready for your holiday season! And enjoy the famous Scream Farm for some extra spooky Halloween fun.
Lark Ranch
A fall wonderland featuring carnival rides, pumpkin picking, corn maze, jump pillow, mechanical bull ride, pony rides, apple cannon shooting, climbing walls, trampolines, gem mining, and a giant slide. New this year – Highland cows!
Pennsy Trail
Enjoy a scenic walk or bike ride on the Pennsy Trail, lined with historical markers, art, and autumn foliage, stretching from the outskirts into Greenfield’s downtown.
James Whitcomb Riley Boyhood Home & Museum
Step into the life of Indiana’s famed “Hoosier Poet” and explore his early years at this homestead‑turned‑museum.
Downtown Greenfield Shopping and Dining
Wander charming Main Street, exploring unique boutiques, antiques, dining, and artisan makers like J. Evelyn Confections within Greenfield Chocolates. And don’t miss the beautifully preserved architecture in the Courthouse Square and residential historic districts. Dine in a restored 1906 grain elevator at The Depot or unwind with craft ales, seasonal brews, trivia nights at Wooden Bear Brewing Co.
H.J. Ricks Centre for the Arts
Catch live performances, indie films, or comedy shows in this art‑deco gem with a gallery and strong community vibe.
Hitherto Coffee & Gaming Parlour
Cozy up with a specialty autumn coffee beverages and a tabletop game or two—perfect for chilly fall afternoons.
Beckenholdt Park
A hidden gem with native prairies, wetlands, walking trails, and a peaceful pond—an ideal spot for a relaxing autumn stroll.
