Don’t Miss These October Events Around Boston

Fall is finally here, and it’s a wonderful time of year to get outside, enjoy the weather and foliage, and have some fun as a family. Check out our list of autumn events and activities happening around Boston in October 2022.

Halloween on the Hill at Long Hill
When: Wednesdays through Sundays starting 9/30/22 and ending 10/31/22
Where: Long Hill–572 Essex Street, Beverly, MA
Age: all ages
Cost: Adults $27/$22, Children (Age 3-13) $10, Children under 2 free
Long Hill is very excited to announce a special new event, Halloween on the Hill! Come explore our beautiful property as we transform Long Hill into a celebration of autumn and the Halloween season. Follow our seasonal-themed trail that will feature over 1,000 jack-o’-lanterns, hundreds of mums and pumpkins, elaborate Halloween sets, light displays, music, and more. This is the perfect Halloween event your family won’t want to miss! Hot cider and fall treats will be available for sale on-site, but tickets must be purchased ahead of time.

The Incredible Naumkeag Pumpkin Show
When: Wednesdays through Sundays starting 9/30/22 and ending 10/31/22
Where: 5 Prospect Hill Road, Stockbridge, MA
Age: all ages
Cost: Adults $27/$22, Children (Age 3-13) $10, Children under 2 free
The Incredible Naumkeag Pumpkin Show is back! This year with more pumpkins, more fun, and an expanded schedule. Explore our famous gardens as we transform Naumkeag into a celebration of autumn with over 1,500 jack-o-lanterns, hundreds of mums, pumpkins and countless gourds – most of which were grown right here at Naumkeag. Advanced purchase of timed tickets is required. Hot cider and fall treats will be available for sale.

The Topsfield Fair
When: Friday 9/30/22 through Monday 10/10/22
Where: Rt. 1, Topsfield, MA, 01983
Age: all ages
Cost: $15 weekdays; $20 weekends/holidays
As far as October events go, this one is a classic. The Topsfield Fair, America’s oldest and finest agricultural fair, has run every fall since 1818. The fair features Fiesta Shows’ carnival midway, The Grand Parade, demonstrations (ranging from beekeeping to miniature trains), a Grange Museum, pumpkin weigh-offs, many musical acts and attractions, the 4-H Agricultural/Arts and Crafts exhibits and so much more. Any list of October events would not be complete without the Topsfield Fair!

Milford NH Pumpkin Festival
When: Friday 10/7/22 through Sunday 10/9/22
Where: Union Square, Milford, NH
Age: all ages
Cost: donations appreciated
The Annual Milford, NH Pumpkin Festival features 3 days of fun, flavor, and festivities. Enjoy musical entertainment on The Oval Stage and the many great vendor booths around The Oval. Pumpkin Carving & Community Lighting On The Oval to be held on Saturday October 8. Carve a pumpkin at our pumpkin carving table Saturday 11:00 AM to 5:00 PM and bring your creation to the community lighting @ 6PM on the Bandstand. Every pumpkin brought to the lighting earns a raffle ticket for our drawing for a pumpkin carved by Jim Flis.

Davis Farmland Corn Maze & Mega Farm Festival
When: Saturday 10/1/22 through Sunday 10/30/22
Where: 142 Redstone Hill, Sterling, MA
Age: all ages
Cost: approximately $40 per person
Over 50 family fun attractions from knocker soccer and quad carts to corn cannons and archery tag OR simply sit back, relax and listen to some live music. Jam out to the areas best local musicians. Dance, sing and be merry. Enjoy a great view of the bands from our lounge-able yard chairs. Enjoy award-winning Kansas City BBQ, savory smoked foods, sweets, treats, and so much more.

Frightful Fridays at Gore Place
When: Fridays starting 10/14/22 and ending 10/28/22
Where: 52 Gore Street, Waltham, MA
Age: ages 6 and up
Cost: $21 general admission
Gore Place’s popular Halloween season program Frightful Fridays returns in October. Enjoy spooky tales, but nothing too scary! The 45-minute program, which features five stories, occurs twice per evening at 6:30 p.m. and again at 7:45 p.m. Capacity is 60 people per session. This program is for adults and children, ages 6 and up. Please, no younger children. The event takes place outdoors under the spacious Century Tent. Tables and chairs will be provided. The site is accessible, and modern indoor restrooms will be available. Dress for the weather. Advance tickets required.

Pumpkin People in the Park
When: Friday 10/14/22 through Monday 10/31/22
Where: Kate Gould Park, Main Street, Chatham, MA
Age: all ages
Cost: free
Pumpkin People in the Park can be found in Kate Gould Park and the bandstand on Main Street in Chatham. The creative and innovative Pumpkin People are fashioned by local businesses, organizations or just plain folk. They are on display from October 14-31! Come and see these outrageous displays in October.

Allison Green
Boston Tutoring Services