Discover Fall Farms and Festivals in Central Massachusetts

By Andrea McHugh; sponsored by Discover Central Massachusetts

While Central Massachusetts has plenty of fall foliage to dazzle visitors, what lingers in the hearts of those who come to explore this region is not only what they see, but also what they experience: picking apples in a family-owned orchard, chatting with local farmers over their harvest bounty, joining in the fun at a small-town fair. From the verdant Blackstone Valley and historic Sturbridge to the renaissance city of Worcester, aka “the Heart of the Commonwealth,” autumn in Central Massachusetts offers no shortage of things to do, and endless memories to be made.

Fall Farms

At this time of year, the excitement of harvest season is felt throughout Central Massachusetts but perhaps nowhere more so than at local orchards, where apple picking, warm cider doughnuts, and hayrides put smiles on the faces of visitors young and old.

Join in a generations-long tradition of harvesting your own apples at Brookfield Orchards, a family-run farm for over a century. With more than a dozen varieties ripening throughout the fall season, you’ll easily load up on the perfect fruit for your pie- or pastry-making endeavors (or just leave the baking to the experts, whose golden-crusted apple pies and other fresh-baked indulgences are also on offer here). The on-site Country Store is a nod to nostalgia, with shelves stocked with honey, jams, jellies, and other locally made goodies — but you may be tempted to hurry up your shopping once you catch a whiff of Brookfield Orchards’ homemade hot apple dumplings.

Set on a pastoral swath of land that’s been farmed since the 1700s, Douglas Orchard & Farm delights families with the sight of ducks, chickens, bunnies, and other barnyard residents against the backdrop of its cozy, classic barn-red Country Store. Farmer Nick Socrat’s passion for organic and sustainable agriculture shows in the plump apples and blueberries grown here (don’t miss the homemade blueberry jam!), along with veggies and herbs in abundance, and even shiitake mushrooms. There’s also a music pavilion serving up live entertainment at the annual Halloween Festival (Oct. 22), featuring a kids’ scavenger hunt, a dog costume parade, Merlin the Talking Witch, and more.

For an unforgettable farm adventure, there’s nothing like navigating the twists and turns of a corn maze. You’ll find an impressive labyrinth of lefts and rights at Wojcik’s Farm in Blackstone, whose five-acre puzzle boasts a celestial theme this year, as well as at Fay Mountain Farm in Charlton, a lovely town-owned property that also offers a more linear option for strollers in the form of the Midstate Trail, which runs through the farm’s 65 acres. That said, any Central Massachusetts farm you visit this fall is bound to have its own unique attractions — from farm wagon tours and complimentary milk and cookies at Whittier Farms in Sutton, to ice cream and pick-your-own pumpkins at West End Creamery in Whitinsville.

Speaking of unique, a short drive from downtown Oxford will bring you to Crown & Roots Farm’s self-serve roadside farm stand, where the array of organically grown veggies is complimented by breathtaking fresh-cut bouquets — yes, you can still find farm-grown flowers in autumn! This time of year, dahlias are plentiful and fill the farm stand with a rainbow of hues. After loading up on home-grown goodies, you just plunk your cash into the old-fashioned “honor” till or, for a more modern spin, opt to pay via Venmo.

Another agricultural standout is the Daniels Farmstead Farmers’ Market, held at a lovingly preserved farm complex in Blackstone that offers a glimpse into rural life over the course of two centuries. Held every Sunday from 11 a.m. to 2 p.m. through October 2, the farmers’ market draws local vendors selling everything from hand-grown produce to fudge, pickles, candles, and even pet accessories. After filling your shopping totes, relax at one of the picnic tables, enjoy some live music, and soak up the atmosphere of a special place that’s been frozen in time.

It’s worth noting that, like Daniels Farmstead, many Central Massachusetts farmers’ markets keep going past summer and into fall — sometimes as late as November. For help finding a cornucopia of local produce that lines up with your travel route, check out this guide to farms and farmers’ markets in Central Massachusetts.

Fall Fairs & Festivals

There may be no better way to feel welcomed into the autumn scene of Central Massachusetts than to mingle with friendly residents at one of the region’s many community events. And no matter if you’re into antiques hunting, apple pies, Ferris wheels, or local brews, there’s bound to be something you’ll want to circle on this fall’s calendar.

So many treasure seekers make the pilgrimage to the Brimfield Antique Flea Market that, like a pop star, it’s known simply by one name: Brimfield. Founded more than six decades ago, the event is held three times annually, with the fall show (Sep. 6–11) being the last hurrah of the year. If you are planning to join the shoppers from far and wide in combing through Brimfield’s rare and curious finds, be warned: It’s impossible to do it all in one day, or even two. The smart bet is to book a stay at the nearby Publick House in Sturbridge and give yourself plenty of time to explore. (A tip for when rooms are sold out in the surrounding towns: Look to Worcester’s hotels for drivable convenience plus urban amenities for nightlife.)

The Publick House is also a convenient home base for enjoying Sturbridge’s annual Harvest Festival (Oct. 15–16), which is held on the inn’s grounds as well as on the town common, where you can peruse local art and crafts, tap your toe to live music, and enjoy tasty treats from food truck vendors. Southbridge’s AutumnFest (Sep. 17) has a similar harvest-fun vibe, plus libations from Hardwick Winery and Rapscallion Brewery. Meanwhile, apple lovers will want to beeline it to Wachusett Mountain in Princeton as autumn revelry hits its peak during AppleFest (Oct. 15–16), a weekend featuring apple pie baking and eating contests along with local crafts, a farmers’ market, kids’ activities, and leaf peeping on the SkyRide ski lift. Apples also take center stage at the Dudley Apple Festival (Oct. 1), where warm apple crisp under a mound of vanilla ice cream makes for a fall dessert you won’t soon forget, amid a day filled with family-friendly attractions such as pumpkin decorating, tug-o-war, and a petting zoo.

Among autumn’s most beloved traditions is the country fair, and Central Massachusetts is home to a classic example: the Spencer Fair (Sep. 4–7), which has been going strong more than 130 years. Expect thrilling competitions (tractor pulls, log sawing, a demolition derby) plus 4-H displays, carnival rides, live music, and all the small-town spirit you could wish for. Not that community vibes are limited to small towns, however: For proof, look to New England’s second-largest city, Worcester, and its Out to Lunch Festival and Farmers’ Market series. Held on the Worcester Common on Thursdays through Sep. 8, this merry mix of farmers, musicians, crafters, nonprofits, and food and drink vendors helps make the heart of the city feel like a local hangout.

Last but not least, beer lovers can get their fill in Central Massachusetts with not one, but four variations on the German tradition of Oktoberfest. A few weeks before its AppleFest, Wachusett Mountain in Princeton kicks off the autumn fun with a two-day Oktoberfest filled with German music and dancing, contests, crafts, and beer (Oct. 1–2); that same weekend, Sturbridge’s Rapscallion Pub holds its annual Oktoberfest celebration at Brimfield Winery & Cidery, with food trucks and live music alongside local brews and wines. Staying close to the city? In Worcester, Oktoberfest comes to you via Wormtown Brewery (Sep. 17), which last year opened a spacious new taproom on Shrewsbury Street, and the Canal District’s Bay State Brewing (Sep. 21), which was actually founded by a pair of German-beer-loving friends in 2012. Prost!