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Perfect Fall Outings for Bostonians 2020

Here are a few places to enjoy socially distanced autumnal fun in southern New England.

New England is a great place for fall fun! Between the leaf peeping, apple orchards, and pumpkin patches, there are activities for the whole family.

Discover Fantastic Fall Fun in New England

Here are a few places to enjoy socially distanced autumnal fun in southern New England.

Belkin Family Lookout Farm

Pick, eat, and play at Lookout Farm, just 30 minutes from Boston. It’s one of the oldest farms in the country, but they’ve kept the place modern by building a taproom and hosting weekend pop-up events in collaboration with local businesses. This year, their U-Pick apple experience is by reservation only. Check their website to see which apple varieties are available for picking each day. Fresh cut pumpkins are available as well. After picking a half peck of fresh fruit, visit the outdoor dining facility featuring a full, all-day menu from 11:30 am to 8 pm Enjoy the sunshine with a classic grilled cheese with frozen grapes, New England lobster roll, or stout grilled beef tips. Finish off the meal with the Lookout Farm cider donuts served with caramel and vanilla ice cream. The curbside market is a great place to take a piece of the farm home. The taproom (using their fruit processed in the solar-powered cidery) sells hard ciders, beer, and bake-your-own donuts kits to go. The barnyard play area, farm animals, and train ride are closed until further notice due to COVID-19 restrictions.

Westward Orchards

Only 45 minutes from Boston in Harvard, MA, Westward Orchards is open for pick-your-own experiences seven days a week. PYO bags are sold from 10 am to 4 pm and no reservations are required. Visit their website for which apples are at peak freshness and ready for picking. Pumpkins have been pre-picked and are conveniently available at the orchard store. There’s a tent set up alongside the porch for guests to enjoy apple cider and donuts in the open air right there in the orchard. Pies, butternut squash and apple soup, locally grown produce, meats, eggs, and cheese are available for curbside pickup as well. Locals can join their CSA program (now in its 9th season) to get the freshest local ingredients. With flexible pickup times and an opportunity to supplement shares with extra Westward Orchard products for a 15% discount, the CSA is an incredible way to support local agriculture while putting the freshest food on the table. They even include recipes to help CSA members get the most out of each farm box.

Only 45 minutes from Boston in Harvard, MA, Westward Orchards is open for pick-your-own experiences seven days a week | WhereTraveler
(Courtesy Westward Orchards/Instagram)

Nashoba Winery

For a more adult weekend, grab a designated driver and visit Nashoba Winery (just over an hour from Boston). Visitors can still enjoy wholesome, pick-your-own fun (check their website for what’s picking each week) or they can make a reservation to visit the picnic grounds Thursday-Sunday. Orders for picnic table delivery can be placed in advance and the menu has something for everyone. Order wine by the bottle, flights, beer, and food from Smith’s Cheese and Stonewall. For those looking for something a little harder, the onsite distillery makes some of the best pear brandy in the area. Want to get involved in the winemaking business? Become a vintner for a day and join in the Reisling harvest this fall. Limited tickets are available for $40 per person. 

Connors Farm

The whole family will enjoy an excursion to Connors Farm. This year’s corn maze is music-themed and open through November 1. Find your way through music notes and instruments before stopping by the farm stand for some of the freshest produce in Danvers, MA. Unfortunately, Hysteria, the Connors Farm haunted experience, is closed until October 2021 due to COVID-19. The Country Kitchen is open seven days a week. Try the hot apple cider donuts that are made fresh daily or indulge with an apple cider slush! On weekends, vendors come by for pop-ups including Bob’s BBQ Pit, Pappy’s Smokehouse, and Grandma’s Sweet Shop. 

Shelburne Farm

Shelburne Farm has one of the largest selections of pick-your-own apples in the area. They offer more than 10 varieties to choose from and their pumpkin patch is PYO too. The farm is open seven days a week, rain or shine, and warm cider donuts are baked fresh daily. The whole family can visit the barnyard to meet the animals and the tractor playground has reopened. Local musicians play live on the weekends and farm employees demonstrate antique cider presses for curious crowds. Visit the bakery to take a bit of the farm home with you in the form of caramel apples, apple squares, coffee cake, or peach bars. The hand-dipped caramel (or fudge dipped) apples can be personalized with a variety of toppings, ribbons, and handwritten tags.

Shelburne Farm has one of the largest selections of pick-your-own apples in the area | WhereTraveler
A pair of children make their way through the maze at Connors Farm in Danvers. (©John Tlumacki/Boston Globe Staff)