Things to do Near You – October 2023

A Local’s Guide to Fall Festivities in Central Mass

While our state is most famous for the hustle and bustle of Boston, Central Massachusetts is a hidden gem full of fun, festive activities to kick off New England’s favorite season! From hometown digs to craft breweries, gorgeous hikes, and more! If you’re looking for fun things to do this month- we’ve got you covered! So pull out your cozy sweaters, dust off those Carhartt beanies, and dive into our roundup of the best autumn activities near you!

Sweet Treats and Good Eats

Do you fancy yourself a bit of a foodie? Or maybe you’re just tired of the clean-up after a good, home-cooked meal? Have the best of both worlds at Cottage Restaurant in Ayer, MA! This local favorite dishes up delicious pizza and subs that will satisfy even the pickiest of eaters. Plus, their ice cream and milkshakes are to die for! If you’re cruising down Main St. in Ayer, be sure to stop into Cottage Restaurant for a meal you won’t forget!

Bonsai and Brews

Pick up a new hobby while sipping delicious, local beer at Dirigible Brewing. On October 4th, Dirigible Brewing will host Bonsai Bar, a beginner-friendly workshop that teaches you the basics of designing and caring for your bonsai tree. Tickets can be found on Dirgible Brewing’s Website. Get yours before they’re gone!


Move over, New York! Central Mass is giving your cannolis a run for their money. Satisfy your sweet tooth at the 7th Annual Cannoli Festival on October 9th in Downtown Leominster! Sample cannolis from local vendors, and enjoy live music as you stroll downtown. There will be fun activities for all ages. This is an event you don’t want to miss.

Foliage Favorites

While it’s still plenty green out, fall foliage is just around the corner! If you’re looking to enjoy the beautiful colors this season is famous for, these local hiking trails are perfect for an autumn stroll:

  • The Nashua River Rail Trail – Bike, Hike, or Ride on Horseback along this 11-mile former railway.
  • Blackman Field and Woods – Just minutes from Gage in Groton, MA, this 48-acre conservation area is the perfect place to explore nature. From scenic views to rocky ledges and gorgeous forests, there’s a trail for everyone at Blackman Field and Woods! Stop by our storefront on your way home for a well deserved post-hike treat!
  • Oak Hill Conservation Land – This nature preserve in Littleton, MA is a family-friendly hiking area with a beautiful lookout spot that’s amazing for an afternoon picnic. With a well-marked trail and gorgeous forests, Oak Hill Conservation will make you want to pack your goodies and head for the hills!

Festive Family Fun

Kick off the fall season with the annual Fall Festival at Hollis Hills Farm in Fitchburg from October 7th-9th. Munch on fresh local apples while you explore the variety of vendors, music, and food at this seasonal staple.

Sale and Swap

Now is the perfect time to get a head start on your winter plans! If new(ish) snowboarding or skiing gear is on your shopping list this year, check out the Wachusett Mountain Sale and Swap from October 5th-9th. Bring in your used equipment and apparel and swap with others. Don’t forget to stop outside for some lawn games and craft brews before you go! Check out the Wachusett Mountain website to sign up and learn more!

And there you have it! A local’s guide to fall fun near you. With so many activities and sites to experience this season, it can be hard to choose from. But, we hope this guide inspires you to get out there and enjoy everything our area has to offer.