October In Guilford: Fall Fun, Festivals & More

Fall is officially here in Guilford, 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 Guilford this October.

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

Guilford Farmers Market

When: Thursday, Oct. 15, 4–6 p.m.
Where: Guilford Fairgrounds, 111 Lovers Lane, Guilford, CT

There’s one more chance to shop the Guilford Farmers Market during a special pop-up market on Thursday, Oct. 15, following the end of its regular 2026 season. Hosted by the Guilford Agricultural Society, the market brings together local farmers, growers, bakers and producers offering seasonal fruits and vegetables, baked goods, artisan breads, meats, seafood, eggs and other specialty products. Shoppers can also find locally made Connecticut crafts at the rain-or-shine market.

Pumpkin Patch Trolley

When: Weekends through Sunday, Oct. 25, plus Monday, Oct. 12, 10:30 a.m.–5 p.m.
Where: The Shore Line Trolley Museum, 17 River St., East Haven, CT

A short drive from Guilford, the Pumpkin Patch Trolley offers a family-friendly fall outing at The Shore Line Trolley Museum on weekends throughout October (plus Monday, Oct. 12). Visitors can ride a historic trolley to the museum's pumpkin patch, choose a sugar pumpkin to take home and enjoy seasonal activities along the way. The last trolley departs at 4 p.m., and tickets are available for individual dates through the museum's website.

Spooktacular On The Green

When: Sunday, Oct. 25, 2–4 p.m.
Where: Guilford Green, Guilford, CT

Celebrate Halloween with an afternoon of family-friendly activities at Guilford's annual Spooktacular on the Green. The festivities will include performers, music and trunk-or-treating, while Guilford Free Library will provide scary stories for visitors who stop by. The outdoor event is geared toward children and families, with no registration required for the library's drop-in activities.

Bishop's Orchards Fall Festival

When: Daily through Sunday, Nov. 1, 10 a.m.–5 p.m.
Where: Bishop's Orchards Main Orchard, 480 New England Road, Guilford, CT

Spend a fall day at the Bishop's Orchards Fall Festival, where seasonal activities include apple picking, a 4-acre corn maze, a pumpkin patch, bounce pads, pedal karts and games. The weekends bring additional offerings, including wagon rides, an apple train, Mega Slide, food trucks and the Cider Hut & Garden serving Bishop's hard cider and wine. Admission options vary by day and activity; pick-your-own produce, pumpkins and certain activities cost extra.

Ghosts Of New Haven

When: Fridays and Saturdays for group tours (private tours available by booking daily), 7:30 p.m.
Where: 1070 Chapel St., New Haven, CT

Take a nighttime walk through New Haven's darker history during Ghosts of New Haven, a recurring tour series. The 90-minute walking tour explores local legends and tales involving historic cemeteries, secret societies, Yale's founders and other reportedly haunted corners of the city. Tours meet outside Starbucks at 1070 Chapel St., with adult tickets starting at $25 and discounted admission available for students, children, military members and seniors.

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

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