If you are looking for some fun New England fall date ideas (or activities with friends), you’ve come to the right place. The fall activities below are perfect whether you are looking for a quick outing or planning a full New England fall getaway. This guide includes all the autumn classics from apple picking orchards to where to stock up on apple cider donuts (plus a whole lot more). Take advantage of New England’s bright foliage by planning a date day with your sweetheart or friends with some of the activities below.
Your New England Fall Bucketlist
- Go apple picking
- Go pumpkin picking
- Drink apple cider or stop by a local coffee shop for a pumpkin spice or maple latte
- Visit a corn maze
- Go walking/hiking in the foliage
- Go camping
- Have a Halloween movie night
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NEW ENGLAND FALL FOLIAGE PEAK PREDICTIONS 2026
Peak fall foliage dates fluctuate each year so the dates below are predictions from various websites. Most of years the best foliage around the Boston area is Oct. 17-Nov. 8.
New England Magazine Peak Fall Foliage Map
https://newengland.com/foliage/foliage/peak-fall-foliage-map
TAKE A WALK & ENJOY THE FOLIAGE IN MASSACHUSETTS
Grab some steamed apple cider or a seasonal fall drink to go from your local coffee shop (if you’re in Boston Pavement Coffeehouse has both) and go for a walk amongst the brightly colored leaves.
Here are just a few recommendations if you are close to Boston: Public Garden, Comm Ave, the Esplanade, Back Bay Fens/Emerald Necklace, Arnold Arboretum (Jamaica Plain), Borderland State Park (North Easton), Blue Hills (Milton), Houghton’s Pond (Milton), Middlesex Fells Reservation (Medford).
GO APPLE PICKING AT YOUR LOCAL ORCHARD
Get outside and enjoy this staple fall activity at an orchard near you. Then once you go picking and bring home your bags cook a recipe together such as making caramel apples, apple crisp, or apple pie.
PICK YOUR OWN APPLES IN MASSACHUSETTS
HONEYPOT HILL ORCHARDS (STOW)
CARLSON ORCHARDS (HARVARD) THEY MAKE THEIR OWN APPLE CIDER WHICH YOU’VE PROBABLY SEEN IN GROCERY STORES
CN SMITH FARM (EAST BRIDGEWATER)
TOUGAS FAMILY FARM (NORTHBOROUGH)
PICK YOUR OWN APPLES IN NEW HAMPSHIRE
CARTER HILL APPLE ORCHARD (CONCORD)
https://www.carterhillapples.com
APPLE HILL FARM (CONCORD)
http://www.applehillfarmnh.com
APPLECREST FARM (HAMPTON FALLS)
MACK’S APPLES (LONDONDERRY)
PICK YOUR OWN APPLES IN VERMONT
SHELBURNE ORCHARDS
https://www.shelburneorchards.com
WHERE TO GO PUMPKIN PICKING IN MASSACHUSETTS
PAKEEN FARM (CANTON)
https://www.pakeenfarm.com/home
WARDS BERRY FARM (SHARON)
HONEY POT HILL (STOW)
CN SMITH FARM (EAST BRIDGEWATER)
GET LOST IN A CORN MAZE
MASSACHUSETTS CORN MAZES
MARINI FARM (IPSWICH)
https://www.marinifarm.com/doggymaze
DAVIS MEGA MAZE (STERLING)
HONEYPOT HILL (STOW)
https://www.honeypothill.com/mazes
CONNORS FARM (DANVERS)
MIKE’S MAZE (SUNDERLAND)
VERMONT CORN MAZES
GREAT VERMONT CORN MAZE (DANVILLE)
https://www.vermontcornmaze.com
WHERE TO BUY APPLE CIDER DONUTS
MASSACHUSETTS: HONEYPOT HILL (STOW), CN SMITH FARM (EAST BRIDGEWATER), PAKEEN FARM (CANTON), TOUGAS FAMILY FARM
NEW HAMPSHIRE: CARTER HILL (CONCORD), APPLECREST (HAMPTON FALLS), MACK’S APPLES
VERMONT: CIDER MILL (WATERBURY)
CONNECTICUT: CLYDE’S CIDER MILL (MYSTIC) THEY HAVE SWEET CIDER, HARD CIDER, AND WINE. IT’S THE OLDEST STEAM POWERED CIDER MILL IN THE UNITED STATES.
IF YOU ARE GLUTEN FREE, DAIRY FREE, OR NUT FREE: YOU CAN BUY PUMPKIN SPICE OR APPLE CIDER DONUTS AT KANE’S DONUTS https://www.kanesdonuts.com/our-donuts/gf-apple-cider
FAIRS & FESTIVALS
TOPSFIELD FAIR OCT. 2-12TH 2026 (TOPSFIELD, MA)
THE BIG E FAIR SEPT. 18TH-OCT. 4 2026 (WEST SPRINGFIELD, MA)
FRYEBURG FAIR OCT. 4-OCT. 11TH 2026 (FRYEBURG, MAINE)
CHAMPLAIN VALLEY FAIR AUG. 8- SEPT. 6TH 2026 (ESSEX, VERMONT)
https://champlainvalleyfair.org
WELLFLEET OYSTERFEST OCT. 17TH & 18TH 2026 (CAPE COD, MA)
https://www.wellfleetoa.org/wellfleet-oysterfest
APPLEFEST WACHUSETT MOUNTAIN WEEKEND 1 OCT. 17TH & OCT. 18TH, WEEKEND 2 OCT. 24TH & OCT. 25TH 2026 (PRINCETON, MA)
https://www.wachusett.com/events/applefest-weekend-i-2026
https://www.wachusett.com/events/applefest-weekend-ii-2026
SALEM FOOD TRUCK & CRAFT BEER FESTIVAL SEPT. 19 & SEPT. 20TH 2026 (SALEM, MA)
https://www.foodtruckfestivalsofamerica.com/salem
WATCH A CLASSIC HALLOWEEN MOVIE
Grab a blanket and watch one of these classic Halloween movies whether snuggled up inside or with an outdoor projector in your backyard. Some all time favorites include the following: Hocus Pocus, The Night Before Christmas, Casper Meets Wendy, and Halloweentown.
VISIT A PUMPKIN DISPLAY
JACK-O-LANTERN SPECTACULAR
I’ve done this event twice and it’s so fun! Located at the Roger William’s Park Zoo, their Jack-O-Lantern Spectacular runs Oct. 1-Nov 1 2026 (this does not include animal exhibits).
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