Ten New England Cities to Explore during the Fall Season

| | | | | | | | | | | | | | | | |

There is no more magical place (IMO) to be during the fall season than New England. (Sidebar: Although, I would probably say that for every season!). Many people descend upon New England towns for the foliage, the festivals, and the food!.And while those are great reasons to visit, they won’t necessarily keep your kids as engaged as you might hope. A couple of years ago we shared this post about specific fall themed activities kids will love (and they ALL still hold true!) but this week we thought we’d share some places that have multiple activities the whole family will enjoy (and we’re including our “neighbors” in New York for a couple of bonuses.) These cities offer year round activities, but the beauty of fall is abundant in all of these spots. 

  1. Bar Harbor, Maine:
    Location: Mount Desert Island and Bar Harbor are located in the easternmost part of Maine, three hours northeast of Portland, under five hours north of Boston, and just over two hours from the Canadian border.
    Little kids will love the Junior Ranger programs and earning a badge.
    Older kids will love Jordan Pond, Bar Harbor Island, and the lighthouse.
    Travel Tips: Bar Harbor is home to the only National Park in New England- Acadia. Acadia is the major draw to the area, but there are plenty of shopping and dining options in the downtown area.
    Read our full Acadia National Park Guide here.
  1. Woodstock, Vermont:
    Location: Central Vermont;  2.5 hours from Boston and Hartford; 4.5 hours from Manhattan
    Little kids will love the animals at Billings Farm and Museum and Sugar Bush Farm, and the science experiments at the Montshire Museum of Science.
    Older kids will love sampling maple sugar at Sugar Bush Farm and the Forest Canopy Walk at VINS.
    Travel Tips: Woodstock, Vermont and Hanover, New Hampshire (home to Dartmouth College) are 30 minutes apart and offer tons of family friendly attractions both indoors and outdoors. Take advantage of the many public hiking places for fall foliage and couple hiking with some of the more kid friendly places in our City Guide. Most attractions have regular hours through October, but check websites to be sure. 
    Read our full City Guide here and our dining in Woodstock guide here.
  1. Portsmouth, New Hampshire:
    Location: The seaside town is just over an hour north of Boston, an hour south of Portland, and three hours east of Woodstock.
    Little kids will love the Children’s Museum of New Hampshire and SeaCoast Science Center.
    Older kids will love Strawbery Banke Museum (open through October and in December for holiday festivities) and the USS Albacore ship.
    Travel Tips: Plenty of metered street parking and garages in the downtown area; check out GoPortsmouthNH.com for up to date information in events and programs.
  1. Gloucester, Massachusetts:
    Very northeastern Massachusetts; 45 minutes from Boston; 90 minutes from Providence
    Little kids will love Maritime Gloucester, Stage Fort Park, and a whale watch tour.
    Older kids will love Cape Pond Ice and Hammond Castle Museum,.
    Travel Tips: Head to DiscoverGloucester.com for up to date info on special events and programs and dining options. Take advantage of the beauty of fall by walking the HarborWalk path and enjoying the beaches without the crowds. On street parking and public lots are far more accessible during calmer fall months. Take note of hours of admission at local attractions as some places are more restrictive during “off peak” season. 
    Read our full City Guide here.
  1. Salam, Massachusetts:
    Location: Northeast Massachusetts, 30 minutes north of Boston, an hour south of Portsmouth, and 90 minutes north of Providence. 
    Little kids will love Salem Pioneer Village and Salem Maritime National Historic Site.
    Older kids will love every witch themed museum, including the Witch Dungeon Museum, the Salem Witch Museum, the Witch History Museum, and the Witch House.
    Travel Tips: Best known for the infamous Salem Witch Trials, the area sees its most visitors during September and October, so be prepared for crowds; there is limited street parking- best to stick with the South Harbor Garage; check out Salem.org for up to date info on special events and programs. 
    Read our full City Guide here.
  1. Berkshires, Massachusetts:
    Location: The Berkshires, comprising over 30 towns and two cities, is located in the most western part of Massachusetts. It includes towns ranging from Sheffield and Great Barrington in the southern part of the state, bordering Connecticut, to the towns of Wiliamstown and North Adams in the northern part of the state, bordering Vermont.
    Little kids will love Berkshire Botanical Garden, Hancock Shaker Village, and the Berkshire Museum.
    Older kids will love The Mount, the adventure park at Jiminy Peak Resort, and tons of great spots to eat!
    Travel Tips: You’ll definitely need a car to explore the various towns; fall is the most popular time for visitors to the Berkshires (leaf peepers!), so be prepared for crowds at popular areas; consider a stay at the Jiminy Peak Resort- so many fun activity and great amenities (open year round, too!)
    Read our full City Guide here.
  1. Springfield, Massachusetts:
    Location: Western Massachusetts, 30 minutes north of Hartford, 90 minutes west of Boston, 2.5 hours southwest of Portsmouth.
    Little kids will love the Dr. Seuss Museum and Yankee Candle Village
    Older kids will love the Basketball Hall of Fall and nearby New England Air Museum (technically in Windsor, CT)
  1. Providence, Rhode Island:
    Location: The capital of Rhode Island is located in the northeastern part of the state, an hour south of Boston and 90 minutes east of Hartford.
    Little kids will love everything at Roger Williams Park and especially the Zoo, and Providence Children’s Museum.
    Older kids will love activities at the Providence Rink, the RISD Art Museum, and exploring the campuses of Brown University, RISD and Providence College (and probably Providence Place Mall). 
    Travel Tips: Make time to go to Federal Hill for authentic Italian food; mostly metered street working (some garages); check the schedule for local sports teams at the Dunkin’ Donuts Center.
    Read our full City Guide here.
  1. Newport, Rhode Island:
    Location: The seaside city is just over 30 minutes south of Providence and 90 minutes south of Boston.
    Little kids will love Fort Adams and many outdoor beaches, parks, and nature centers, including the Sachuest Point National Wildlife Refuge.
    Older kids will love the International Tennis Hall of Fame, Audrain Car Museum, and Thames Glass. 
    Travel Tips: Newport is most famous for the Gilded Age mansions, many of which are open to the public for tours and special events. Kids might not be as engaged as adults for these tours but The Breakers has a great kid focused tour; Newport is much calmer and quieter in the “off season” months; best parking option is the garage next to the Visitor Center. 
    Read our full City Guide here, our holiday guide here, and our hiking guide here.
  1. Mystic, Connecticut:
    Location: The seaside town is located in the easternmost part of Connecticut, on the very end of Long Island Sound, one hour southeast of Hartford, three hours north of Manhattan, and two hours south of Boston.
    Little kids will love Mystic Aquarium and Denison Pequotsepos Nature Center.
    Older kids will love Mystic Seaport, Fort Griswold and Fort Trumbull, and the ice cream trail!
    Travel Tips: A Visit to Clyde’s Cider Mill is a MUST during the fall season; make sure to have a meal at a spot with a waterview (so many yummy choices!) 
    Read our full City Guide here and our hiking guide to Mystic here.

Two bonuses: Technically, New York isn’t part of New England, but we enjoyed these parts of the Empire State so much (and they are closer to many New England location than other spots on our list) that we thought we would highlight them in this post:

  1. Lake Placid, New York:
    Location: Located in northern New York, Lake Placid is 2.5 hours north of the state capital of Albany, and three hours northwest of Woodstock, Vermont.
    Little kids will love Santa’s Workshop (open on weekends in September and early October); Adirondack Experience, the Museum on Blue Mountain Lake; and The Wild Center
    Older kids will love all the Olympic sites and the chance to ride a coaster and a zipline.
    Read our full City Guide here.
  1. Hudson Valley and Dutchess County, New York
    Location: The Hudson Valley area 
    Little kids (well, everyone!) will love the Great Jack O’Lantern Blaze at Van Cortlandt ManorValley , and Mid Hudson Children’s Museum
    Older kids will love the FDR Presidential Library and Museum, Old Rhinebeck Aerodrome, and the Trevor Zoo
    Read our full City Guide to Dutchess County here.

Check out our full list of City Guides here and follow along on our adventures on Instagram, Pinterest, Facebook, and Twitter.

Similar Posts


  1. We have been wanting to plan a fall trip to New England to see all the fun festivities! Thanks for sharing 10 great cities to explore during the fall. I loved the first photo of you all with the pumpkin! So fun.

  2. We are headed to Connecticut in a few weeks. I am so excited! I love visiting New England in the fall. I’m looking forward to checking out Mystic this year. Thanks for all the suggestions!

  3. We are always looking for new spots to explore and enjoy the Fall activities. It looks like we would we enjoy exploring New England during the Fall season. There are a lot of activities for families of all ages to enjoy in the cities in New England. And enough variety to keep everyone entertained. I love the selection of indoor activities for wet days.

  4. We loved visiting Portsmouth and Newport during our fall trip to New England last year! I would love to check out more of these cities on our next trip. Thank you for sharing! Also, your kids are adorable! 🙂

Leave a Reply

Your email address will not be published. Required fields are marked *