October In Simsbury: Fall Fun, Festivals & More

Fall is officially here in Simsbury, and there’s no shortage of ways to make the most of it. From festivals and farmers markets to pumpkin patches, live music and other seasonal fun, October brings plenty of reasons to get out and enjoy what’s happening close to home.

Here are some events and activities happening in and around Simsbury this October.

Dates, hours and other event details can change. Check with organizers before heading out.

Fall Gather-ing Artisan Market

When: Saturday, Oct. 17, 2026, 11 a.m. to 3 p.m.
Where: Gather On Hopmeadow | 961 Hopmeadow Street, Simsbury

Spend a crisp fall afternoon browsing locally made goods at the Fall Gather-ing Artisan Market at Gather on Hopmeadow. The community event brings together arts, crafts, food and live music for a laid-back seasonal outing. If the weather doesn't cooperate, a rain date is scheduled for Oct. 18.

Tower Toot Festival 2026

When: Oct. 17-18, 2026, 11 a.m. to 4 p.m.
Where: Heublein Tower, Talcott Mountain State Park | Summit Ridge Drive, Simsbury

Fall foliage comes with quite a view at Tower Toot Festival 2026, a two-day celebration held at the summit of Talcott Mountain on Oct. 17 and 18. Visitors can hike approximately 1.25 miles from the parking area to enjoy live music, food and craft beverages while taking in the scenery surrounding Heublein Tower. Admission is free, with food and drinks available for purchase, and proceeds benefit the preservation and restoration of the historic tower.

Halloween Paint & Sip With Deborah Leonard

When: Thursday, Oct. 22, 2026, 6 to 8 p.m.
Where: Simsbury Free Library | 749 Hopmeadow Street, Simsbury

Tap into your creative side with a spooky twist during the Halloween Paint & Sip at the Simsbury Free Library. Local artist Deborah Leonard will lead the evening painting event, which is open to all, but space is limited and advance sign-up is required. Participants should also drop off or mail their participation fee to the library before the event to secure their spot.

Spooktacular 2026

When: Saturday, Oct. 24, 2026, 1 to 5 p.m.
Where: Simsbury Meadows Performing Arts Center | 22 Iron Horse Boulevard, Simsbury

Simsbury Meadows will be filled with Halloween spirit during Spooktacular 2026, a family-friendly afternoon featuring live music, food trucks, games and local vendors. Kids can bounce, trick-or-treat among participating business tents and tables and join in the costume contests, with prizes offered in multiple categories. Costumes are encouraged, so this is one event where dressing for the occasion is part of the fun.

Sensory Friendly Halloween

When: Wednesday, Oct. 28, 2026, 4:30 to 6:30 p.m.
Where: Apple Barn | 60 Old Farms Road, Simsbury

A gentler Halloween celebration awaits families at Sensory Friendly Halloween at the Apple Barn in Simsbury. The free event welcomes kids of all ages for games, giveaways and refreshments in a sensory-friendly setting. Costumes are welcome but not required.

Looking for more things to do in Simsbury this fall? Check out the Patch events calendar for more local events and activities.

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