October has arrived, bringing crisp air, cozy flavors, and plenty of reasons to get out and celebrate fall in Central Massachusetts. From pumpkin-filled festivals to lively trivia nights, this month’s calendar is packed with opportunities to connect with the community, try something new, and soak in the season. Whether you’re looking for wellness activities, local brews, or a night of Victorian enchantment, there’s something happening nearby for every interest.
Chair Yoga for Pain & Stress Relief: Mondays, October 6–27th
Take a midday pause this October with Chair Yoga for Pain & Stress Relief at Dragonfly Wellness Center. This four-week hybrid series (in-person and online) runs Mondays from 12:00 to 12:45 PM, making it easy to fit into your lunch break. Guided by Anita Perry, an award-winning instructor, author, and podcaster with more than 46 years of experience, the class blends gentle yoga, meditation, and Chinese acupressure, all done while seated. It is designed to help ease aches, insomnia, headaches, anxiety, and more, offering practical tools to restore balance and calm. Reserve your spot today and give yourself the gift of relief and relaxation.
Trivia Night:
Tuesdays, October 7-28th
Tuesday nights just got smarter at Sterling Street Brewery in Devens. Their weekly trivia brings rotating categories, audio and picture rounds, and plenty of surprises to keep things interesting. Grab your crew, sip something tasty, and put your knowledge to the test in a fun and relaxed setting. It is always free to play, with prizes awarded each week. See more information here!
Hollis Farm Fall Festival:
October 11–13th
Celebrate the season at Hollis Hills Farm’s annual Fall Festival, happening October 11th, 12th, and 13th from 11 AM to 4 PM each day. This family-friendly weekend has something for everyone, with pick-your-own pumpkins and apples, local vendors, live music, and plenty of specialty food and drinks to enjoy.
On Monday, October 13th, the music lineup features Triple Tribe from 11 AM to 2 PM, followed by the Whitney Doucet Band from 2 PM to 5 PM.
Make a day of it and soak up the best of fall in New England with food, fun, and festivities. See event information here!
Shirley Pumpkin Festival:
Sunday, October 12th
Celebrate fall on the Shirley Center Common at the annual Pumpkin Festival. Enjoy live music from Railroad House, a six-piece Americana band, and take part in scarecrow building or pumpkin carving contests with prizes up for grabs.
Sip a pint at the Sterling Street Brewery beer garden and sample food from local vendors ranging from authentic Mexican and Seoul street food to baked goods, cider, and hearty pub fare. Sponsored by the Shirley Charitable Foundation, this festival is a great way to spend a crisp October evening with friends and neighbors. Learn more here.
MASSive Craft Beer Garden:
Saturday, October 18th
Raise a glass at Leominster’s 3rd Annual MASSive Craft Beer Garden, returning to downtown on Saturday, October 18, from 12 to 4 PM. This outdoor event features an impressive lineup of Massachusetts breweries, including Aeronaut Brewing Company, Castle Island Brewing Co., Dirigible Brewing Company, Distraction Brewing, Lost Towns Brewing, Moon Hill Brewing, and Sterling Street Brewery.
Alongside the beer, guests can look forward to food trucks and live music, with details to be announced soon. Tickets are available online in advance.
Victorian Fairytale Ball: Saturday, October 18th
Step into a storybook evening at the Victorian Fairytale Ball, hosted by Footwork & Frolick at Ayer Town Hall. Inspired by late 19th-century fairy tales and fantasy stories, this whimsical costume ball blends historical elegance with a touch of magic. Guests can expect beginner-friendly dances, live music, and sweet treats in an enchanting atmosphere.
Costumes inspired by fairy tales, fantasy, or Victorian fashion are encouraged but not required—simply wear whatever makes you feel elegant and ready to join the fairy court. For those new to historical dance, all steps will be taught, and no partner is needed. A pre-ball workshop will also be offered in the afternoon for anyone who would like to practice in advance.
Doors open at 6:30 PM, with dancing from 7:00 to 10:00 PM. Whether you are a seasoned dancer or stepping onto the floor for the first time, the evening promises a magical escape into another era. For further event information and ticket sales click here.
This October, Central Massachusetts is alive with events that bring neighbors together and highlight the best of the season. Whether you’re unwinding with yoga, tasting craft beers, or stepping into a fairytale, these gatherings are a chance to celebrate community, creativity, and the beauty of fall.
