The Berkshires Blog

Best Cute Towns to Visit with Kids Near NYC

Some of the best cute towns to visit with kids near NYC await your next family adventure!

Published by Families Travel, May, 2020

Some of the best cute towns to visit with kids near NYC await your next family adventure! With so many New Yorkers searching for their next family-friendly destination, why not consider an adorable vacation town within driving distance? New York’s convenient location puts you within hours of amazing gems in New England, Pennsylvania, and Connecticut, most of which are ideal to visit with children during the summer! From these towns, you can also glean a better idea of some of the best day trips to take, depending on how much time you spend exploring. Next time you’re ready to plan a road trip from New York, check out our list of best cute towns to visit with kids near NYC to arrange your next itinerary!

Great Barrington, MA

Great Barrington is an adorable Massachusetts town! Stroll past restaurants, cute cafes, and quaint shops when you visit its downtown Main Street. Stop in town for some wood-oven pizza at Baba Louie’s while you’re at it! Then, satisfy your sweet tooth at Soco Ice Cream, one of the best dessert places in town. Berkshire Mountain Bakery is amazing for fresh bread, pastries, and pizza baked daily! Great Barrington also has accessible public beaches and swimming holes along the Green River, with opportunities to kayak, paddleboard, etc. For a flat hike with younger kids, head to Housatonic to stroll right along the river. Beartown State Forest also offers various trails and activities on Benedict Pond like swimming, boating, or fishing. Adventurers will also race to Catamount Aerial Park, featuring zip-lining and obstacle courses. In Lee, hike the Appalachian Trail through October Mountain State Forest. In addition to summer activities, Great Barrington is also great to visit for winter skiing.

Great Barrington also puts you near other Massachusetts destinations. Take a day trip to Westfield, and kids can spend a rainy day at the Amelia Park Children’s Museum. Or, spend a sunny afternoon roaming free in Stanley Park. In North Adams, older kids with a more refined interest in art may particularly benefit from a visit to the art museum Mass MoCA. (Be sure to drive through the historic Hoosac Tunnel!) During the summer, Jiminy Peak Mountain Resort also showcases plenty of ways to stay cool, including a Mountain Adventure Park! In Stockbridge, tour pristine estate and gardens at Naumkeag, featuring views overlooking Monument Mountain. Or, visit the Edith Wharton Mansion in Lenox, once home to a famous American author. Drive to reach the Connecticut border and you can also visit Bash Bish Falls in Mount Washington State Park, one of the tallest waterfalls in Massachusetts.