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Guide To Enjoying A Perfect Fall Day In New England

The fall season in New England is simply perfect: warm, gentle sunshine and near perfect temperatures for outdoor adventures. Bask in the glow of fall in Boston with apple picking, al fresco dining, hayrides and foliage-fueled drives. Use this guide to make a day of frolicking this fall. 


(Photo credit: KIMIHIRO HOSHINO/AFP/Getty Images)

Honey Pot Hill Orchard
138 Sudbury Road
Stow, MA 01775
(978) 562-5666

It’s nearly impossible to live in New England and not apple pick in the fall. With farms in every corner of Massachusetts, it's easy to enjoy the fruits of your own labor. Honey Pot Hill has long been popular for families with small children. Offering hayrides, an excellent selection of apples for picking, pear picking, a hedge maze, and of course - cider donuts, Honey Pot doesn't disappoint. Small children especially love the orchard's mascot, Henry the bear. Honey Pot Hill Orchard is about a 45-minute drive from Boston. For a quick guide to selecting other farms, see a Guide to Apple Picking in Boston. Many farms included in the guide also offer hayrides, which are perfect for any age.

Big E Fair
(Photo Credit: Big E/Facebook)

The Big E
1305 Memorial Ave.
West Springfield, MA 01089
(413) 737-2443

Running from Sept. 14 to 30, the Big E is a family friendly, annual New England states fair in West Springfield. Known for its unique exhibits, fair rides, farm animals and fair food, the Big E is a staple for outdoor fall fun. Two must eats: a loaded baked potato from the Maine state building, and the infamous Big E cream puff. Weekends are extremely busy here, so try to visit during the week if your schedule permits. 

fall weather
(Photo by Oli Scarff/Getty Images)

Foliage Along Route 2
Boston suburbs, MA

There is nothing like the contrast of autumn colored leaves against a blue sky or a body of water. While there are options for viewing leaves both by car and by foot, consider taking a drive out to western Massachusetts along Route 2. A trip along this route yields picturesque views of New England towns set against a color-filled foliage backdrop. 

Related: Guide to Enjoying Fall Foilage in Boston


Charles River Kayak
1071 Soldiers Field Road
Boston, MA 02134
(617) 462-2513

Kayaking is not just a summer activity, and you can easily enjoy this outdoor activity well into the fall. With five locations in the greater Boston area, Charles River Kayak makes it easy and convenient. In addition, options for evening rentals are available to catch the sunset shining through vibrant leaves as the days shorten. Be sure to review the website for information about late afternoon and moonlight tours, which are a relaxing way to enjoy the sunset against the foliage and water.

Legal Harborside @ Night
(Credit: Legal Sea Foods)

Legal Harborside
270 North Ave.
Boston, MA 02210
(617) 477-2900

A recent addition to the waterfront dining scene, Legal Harborside offers three floors of dining with two providing the option to dine outdoors. While Legal has other locations around town, the views from the Harborside location can't be matched. Make reservations early for the highly coveted roof deck. If the roof deck is full, opt for the smaller outdoor dining area on the first floor.

tavern on the water via facebook
Photo Credit: Tavern On The Water via Facebook

Tavern on the Water
18th Street 6 
Charlestown, MA 02129
(617) 242-8040

There’s no shortage of outdoor seating or views of the Boston skyline from this Charlestown eatery. If you're not able to visit for dinner, try stopping by in the morning for the brunch menu. Tavern on the Water is conveniently located near the Charlestown Navy Yard. If you stop by early enough, you can potentially make an afternoon of your trip and visit the nearby yard. 




Cristy is a city dwelling enthusiast, an arts, culture, and technology lover, and an all around curious person. As an examiner, she covers all things Boston. Her work can be found on

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