An Exciting Tour Through Massachusetts’s Finest Breweries, Wineries, and Orchards

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Coming to Massachusetts this autumn? Following a few days of admiring the lush fall foliage in the Berkshires and some urban fun in Boston, there's nothing more enjoyable than touring the state's finest breweries, wineries, and orchards.

No matter what you're after, they offer endless fun for both adults and families. Picture yourself drinking an ice-cold beer with friends around a fire pit or following your little ones picking apples around an orchard, these are the kind of fall memories you’ll treasure forever.

Oak Realty has compiled a round-up of Massachusetts’s best breweries, wineries, and orchards for some fall fun.

Nashoba Valley Winery

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Photo credit: Nashoba Valley Winery

Come and pair some apple picking with flavorful wines at Nashoba Valley Winery. Situated in the town of Bolton, Nashoba Valley Winery spans over 50 acres and features an expansive orchard and vineyard, a modern winery, a distillery facility, and two upscale eateries.

Your visit to Nashoba Valley Winery will likely begin with a wine tasting in the pavilion, where a wide array of wines awaits you. As you sip through the menu, the kids will be kept busy with an afternoon of apple picking, then refuel together at J’s Restaurant, with a menu filled with dishes made with local farm products.

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Pam - “A fig and grilled cheese sandwich and a glass of Cranberry Apple wine at Nashoba Valley Winery makes my Saturdays so much better.”

Clover Road Brewing Company - Ashland

Clover Road Brewing Company's location in Ashland is every beer lover's dream. With a frequently updated selection of brews on draught, those who value high-quality pints will appreciate their line-up, particularly the Backhouse Hazy IPA that bursts with fruity notes and the malty Operation Stein Grab.

Anyone who's been here during fall before knows that the outdoor patio is a hit, especially when they get the fire pit going. Best of all, even if you have youngsters, they’re welcome to come along, as there are plenty of games to keep them entertained.

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Steve - “Sitting outside by the firepit at Clover Road Brewing Co with a pint of Operation Stein Grab Märzen is exactly how I want to spend a cool fall evening.”

Start Line Brewing

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Photo credit: Start Line Brewing

Hopkinton's Start Line Brewing has long been loved by beer fans since it opened in 2016. From an extensive menu with 18 tasty brews to scrumptious grub like slow-smoked brisket, this is a brewery where it's all about sharing good food with even better pours.

Whenever there's a live music event planned, the outside area comes alive with different bands playing while customers have an epic view of the Hop Yard. Try to arrive early, though, as they don't accept any table bookings.

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Ed - “I love sitting on the patio at Startline Brewing Co with a Jack’d Pumpkin Ale and catching a band. Fall doesn’t get better than that.”

Honey Pot Hill Orchards

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Photo credit: Honey Pot Hill Orchards

A sprawling 186-acre orchard filled with apples, peaches, and blueberries when fall arrives, Honey Pot Hill Orchards in Stow has been around since 1926. At the Martin family's orchard, daily apple picking is open to everyone, just purchase a bag, and that covers your entry.

There's also a bunch of entertaining activities here for children, including hay rides, farm animal viewings, and much more. Don't forget to try their cider donuts and stop by their farm store before heading home. They've stocked all sorts of fresh produce, including Bartlett pears.

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Gretchen - “Honey Pot Hill has the best cider donuts in Massachusetts, and you’ve got to try the Spencer apples.”

Lookout Farm Brewing & Cider Co.Taproom

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Photo credit: Lookout Farm Brewing & Cider Co.Taproom

Want to try some delicious cider? Look no further than Lookout Farm Brewing & Cider Co.Taproom in Natick. Their orchard with Asian pears and Honeycrisps provides the backbone of each refreshing pour of cider.

Families can pick up the Half Peck Picking Bag & Wristband for the kids, allowing them to use the corn maze, tractor play area, and other facilities. Meanwhile, parents can relax in the taproom, cider in hand, listening to live music with the orchard as the backdrop.

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Laura - “A flight of seasonal hard ciders from the Taproom with a plate of farm-to-table brisket overlooking the orchards makes any fall day the best.”

Vanderwalk Farm & Winery

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Photo credit: Vanderwalk Farm & Winery

Vanderwalk Farm & Winery has quickly become a Mendon favorite, winning locals over with wines crafted from their own berries. Come fall, you’ll want to try their sangrias or wine slushies, and even your furry friend can join in on the fun with a dog slushie.

On weekends, food trucks roll in, giving visitors the chance to try some tasty bites alongside a blueberry wine mojito or a crisp, chilled beer. At certain times of the year, they host food markets where farmers and artisans come together to showcase seasonal produce.

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Sasha - “My humans bring me to Vandervalk Farm for the dog slushies. They pick apples, sip fruit wine slush flights, and I get to hang with friends -  best day ever.”

Make the Most of Fall in Massachusetts With a Trip to These Breweries, Wineries, and Orchards

It's no secret that Massachusetts is a state with a never-ending list of breweries, wineries, and orchards. Though worth a visit any time, autumn brings an extra layer of charm with seasonal offerings and family-friendly traditions you don't want to miss.