The Small Town In Massachusetts That Comes Alive In The Fall Season
By Kim Falchek|Published September 26, 2023
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Kim Falchek
Author
Kim Falchek has been exploring the towns, trails, and hidden gems of Massachusetts since her college days in Boston. When not writing, Kim enjoys photography, going on road trips, and spending time at the beach. Kim has previously been a contributing writer for LA Family Travel, Global Munchkins, and Latched Mama. She currently lives in Salem, Massachusetts where she and her family embrace all things Halloween!
Fall foliage season is in full swing, and now is the time to hit the road for some prime leaf peeping! Gorgeous yellow, red, and orange leaves are blanketing small towns across the state, providing spectators with spectacular views. We have previously told you about Ipswich, Plymouth County, and many other fantastic places to visit in the fall. A trip to the small town of Stockbridge, Massachusetts’ beautiful fall town, is another autumn experience that you won’t want to miss.
Stockbridge is a quaint little town in the Berkshire region of the state.
While it is a beautiful place to visit year-round, it is particularly breathtaking during the autumn months. The foliage here has been consistently ranked as some of the best in the state.
If your trip to town includes a hike, I suggest checking out the scenic Laura’s Tower Trail. This 1.8-mile moderate trail leads you to a tower where you can climb up and enjoy some beautiful views.
Also known as Lake Mahkeenac, the bowl is a great spot to enjoy some outdoor fun both on and off the water.
One of the town’s biggest fall events takes place at Naumkeag, the former estate of well-known lawyer, Joseph Choate. Throughout the month of October, you can tour the lush property and visit over 1,500 uniquely carved jack-o-lanterns when you attend The Incredible Naumkeag Pumpkin Show.
The museum sits on 36 acres of land. So you can tour the massive collection of iconic Rockwell art inside the museum, and then spend some time admiring the colorful views outside.
Even if you don’t feel like walking, you can still enjoy the majestic foliage of Stockbridge.
Take a scenic fall train trip between Stockbridge and Lenox on the Hoosac Valley Train Ride. Sit back and relax while enjoying 90 minutes of stunning scenery.
There is so much fall fun to experience in Stockbridge that you might as well turn your trip into a getaway.
A stay at the historic Red Lion Inn is the perfect way to make the most of your autumn visit. Spend time relaxing on the front porch and feast on classic American cuisine in the main dining room or Olde English Pub. You can also enjoy delicious cocktails in the inn’s speakeasy.
Have visited Stockbridge in the autumn? What was your favorite place? To find out the best times and places to view the foliage in Stockbridge and throughout Massachusetts, check out our foliage map.
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