October In Barnstable: Fall Fun, Festivals & More

Fall is officially here in Barnstable, 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 Barnstable this October.

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

Harvest Festival Series

When: Saturdays through Oct. 24, 2026, 10 a.m.–1 p.m.; live music continues from 1–4 p.m.
Where: Love Farms | 607 Main Street, West Dennis

Make the trip to nearby West Dennis for the Harvest Festival Series at Love Farms, where each Saturday brings a different seasonal theme. A wristband includes access to tastings, activities, vendors and farm experiences, while face painting, vendor purchases and food specials cost extra. Families can also enjoy farm tours, kids’ activities and live music, and tickets are required for guests ages 3 and older.

Howl-O-Ween Pet Parade

When: Sunday, Oct. 25, 2026, noon–1:30 p.m.
Where: Hyannis Country Garden | 380 West Main Street, Hyannis

Dress up your four-legged friend for the Howl-O-Ween Pet Parade at Hyannis Country Garden. Pets can strut their costumes, follow a trick-or-treat trail and compete for prizes during this festive fundraiser. Registration is $10, with proceeds supporting the Companion Animal Program of Cape Cod and The Sampson Fund for Veterinary Care, and pets should remain on leashes.

Halloween Safe Trick or Treat

When: Saturday, Oct. 31, 2026, 4–6 p.m.
Where: Hyannis Main Street, Hyannis

Celebrate Halloween in the heart of Hyannis during Halloween Safe Trick or Treat. Main Street will close to traffic so families can stroll safely in costume while participating businesses hand out treats along the way. No admission fee is listed, making this an easy local option for families looking for traditional trick-or-treating.

Pumpkinpalooza

When: Oct. 14–Nov. 1, 2026
Where: Kate Gould Park | Main Street, Chatham

Head to nearby Chatham for Pumpkinpalooza, also known as Pumpkin People in the Park, a whimsical seasonal display that fills Kate Gould Park with creative characters. Local businesses, nonprofits and community members build imaginative pumpkin-themed displays that visitors can enjoy throughout the second half of October. No admission fee is listed, so families can stop by while exploring downtown Chatham.

Orleans Farmers' Market

When: Saturdays through November, 9 a.m.–12 p.m.
Where: 19 Old Colony Way, Orleans

Take a trip to nearby Orleans for the Orleans Farmers' Market, a year-round gathering focused on locally sourced food from Barnstable County. Shoppers can browse offerings from Cape Cod farmers, fishermen and food artisans while supporting a market that also accepts SNAP and HIP benefits. The outdoor market runs rain or shine through November, then moves indoors for the winter season.

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

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