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
FALL ROAD TRIP SNACKS
- Apple Cider- You can find some at your local grocery store or orchard to bring along for the drive
- Apple Cider Donuts- You can find some at your local grocery store or orchard (or if you have allergies you can order a box of Freedom Apple Cider Donuts)
- Pumpkin Flavored Drink- Grab a pumpkin flavored latte from a local coffee shop or bring along a NOBL Maple Pumpkin Latte for the road
Table of Contents
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).
BEST LOCATIONS FOR A NEW ENGLAND FALL VACATION
BEST THINGS TO DO IN VERMONT: WHERE TO STAY & ACTIVITIES
PLAN A ROMANTIC VERMONT FALL GETAWAY & STAY AT ONE OF THESE ACCOMMODATIONS
Locals and those from around the world travel to Vermont in hopes of seeing the bright foliage colors so the best course of action is booking your accommodations well in advance. If you can only pick one place to base out of for your Vermont fall getaway then Stowe is going to be your top choice due to its proximity to the mountains.
When to book for Vermont Foliage: Late September-First Week of October
Vermont foliage times can vary year to year but I recommend booking to see peak foliage. It’s always best to look at the New England Fall Foliage Tracker to get real time updates of the current foliage conditions.
Hilton Garden Inn Burlington Downtown – Burlington, VT
Hotel Champlain- Burlington, VT
DoubleTree by Hilton – Burlington, VT
Shelburne Farms Inn – Shelburne, VT
The Lodge at Spruce Peak – Stowe, VT (4 star)
Stoweflake Mountain Resort & Spa- Stowe, VT
Woodstock Inn & Resort – Woodstock, VT
Von Trapp Family Lodge – Stowe, VT
Equinox Golf Resort & Spa – Manchester, VT
The Essex Resort – Essex Junction, VT
Mountain Top Inn & Resort -Chittenden, VT
Castle Hill Resort & Spa – Proctorsville, VT
The Pitcher Inn & Wellness Center – Warren, VT
The Mountain Inn at Killington
Twin Farms – Barnard, VT (the only 5 star hotel in VT)
PLAN A ROMANTIC NEW HAMPSHIRE FALL GETAWAY & STAY AT ONE OF THESE ACCOMMODATIONS
New Hampshire is famous for its vibrant fall foliage. Year after year thousands of people travel to NH to see the colors change and experience New England fall to the fullest. Picture a gorgeous fall day amongst exploding colors of red, orange, and yellow leaves when you look across a mountain valley. You celebrate with apple cider, freshly baked cider donuts, and even go apple picking at a local orchard.
Top tip: In years past the brightest fall foliage in the White Mountains National Forest region occurs the last week of September to October 10th. You can get real time updates on the New Hampshire.gov website.
New Hampshire Fall Foliage Tracker
Mountain View Grand Resort & Spa
Riverwalk Resort at Loon Mountain
Wentworth By The Sea: A Marriott Hotel & Spa
This blog post contains affiliate links so I may earn a commission if you book directly from the links below at no additional cost to you. This is a MASSIVE help as I balance being both a full time photographer while also pursuing my Broadway NYC dreams – so big thanks in advance!
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