best autumn day trips near boston

Best Autumn Day Trips Within 100 Miles Of Boston

Are you ready to take a break from the hustle and bustle of the city? Fall is a great time of year to get out and explore all the sites of New England.

From famed fall foliage to fascinating historical destinations, there are so many places to explore. Here are 9 of my favorite autumn day trips within 100 miles of Boston.


There is no more festive a destination than Salem in the fall. As the sight of the 1692 Witch Trials, it is a popular destination around Halloween. Visit attractions such as the Witch Museum, Witch House, or the Witch Trials Memorial. If witches aren’t your thing, the art exhibits at the Peabody Essex Museum are right around the corner. Don’t forget to grab a bite at the Sea Level Oyster Bar for lunch overlooking the harbor.

fun fall things to see Boston

Plimoth Plantation

A fun destination for adults and kids alike. Journey back in time to the days of the Pilgrims at this living history museum. Here you will find the Mayflower II, a full scale reproduction of the historic ship that carried the Pilgrims to America. You will also find historically accurate representations of the 17th century English Village, Wampanoag Homesite and the Plimoth Grist Mill.


Old Sturbridge Village

The largest living museum in Massachusetts is a must see. Old Sturbridge Village depicts life in early 19th century New England. Take part in a historical craft class or catch a show like the Sleepy Hollow Experience. With over 200 acres of historical buildings, gardens and nature trails to explore, there is plenty to see and do to keep you busy throughout the day.

Walden Pond State Reservation

Just a 35 minute car ride from Boston lies Walden Pond, made famous by Henry David Thoreau’s Walden. Take in the breathtaking Fall Foliage while exploring the park’s 250 acres. Bring your fishing pole, kayak and a picnic lunch and enjoy a day on the shore. Don’t forget to stop by the replica of the cabin where Thoreau lived and worked for 2 years.

Seven Arrows Farmgreat places to see in fall Boston

This little gem is a must see for nature lovers. Stroll through the gardens of uncommon plants, say hello the the animals or just sit and relax with a cup of tea while taking in the beautiful scenery. You won’t want to miss the farm store where you can purchase dried herbs, teas and other unique gifts.

Davis Farmland

Davis Farmland Discover Farm is the perfect family destination. In addition to seasonal events like apple and pumpkin picking, you will also find attractions like the Imagine-Acres play area, a showcase of endangered farm animals, and the Mega corn maze. There is no shortage of things to do and see.

Bridge Of Flowers

An abandoned trolley track converted into a public garden, the Bridge of Flowers in Shelburne Falls boasts several hundred different flowers, shrubs and trees in a rainbow of colors. As you cross the bridge, don’t be surprised if you are greeted by butterflies and hummingbirds. Not only is the bridge itself stunning but the views of the nearby mountains and the deerfield river are unmatched. There are plenty of nearby shops, cafes and restaurants to make it easy to spend the day in the area.

Castle Hill

Why not spend your day leisurely strolling the grounds of a mansion? Castle Hill in Ipswich is a sight to behold. In addition to 59 room mansion, there are 4 miles of trails where you can spot a wide array of wildlife including deer, fox, turkeys, great horned owls and even an occasional bald eagle.

great places to go in fall BostonSandwich Glass Museum

Cape Cod is often thought of as a summer destination, but fall is the perfect time of year to visit the Sandwich Glass Museum. The museum has “Relit the Fires In Sandwich” from the days of the bustling glass industry of old. Watch a live glass blowing demonstration and browse the beautiful glass exhibits which boasts over 6000 unique pieces produced at the Boston & Sandwich Glass Company between 1825 and 1888


Jewell Towne Vineyards

A pit stop at New Hampshire’s oldest winery is the perfect getaway for wine enthusiasts. Set on the shores of the Powwow River, Jewell Towne Vineyards is a charming, rustic destination. Take a complimentary tour around the winery and sample a selection of local wines which have collectively won over 150 awards. This is the perfect romantic getaway for a couple.

If you’re looking for a last minute getaway to recharge and relax, there are plenty of destinations right outside your front door. Where is your favorite place to escape in the fall?

Ruth Malkin Brookline Real Estate Expert