4 Cozy Western Massachusetts Towns You Need to Experience This Fall

Warm sweaters, hot apple cider, colorful leaves, and leisurely strolls are just some of the aspects that attract visitors to Massachusetts during the fall months. There's nothing like taking in the crisp, cool air while having a beautiful outdoor backdrop behind you. Western Massachusetts is the perfect spot for this experience.

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Cozy Western Massachusetts Towns That are Perfect for a Fall Visit

While Western Massachusetts is home to many towns that are ideal for fall exploration, today we're spotlighting four towns you may want to consider exploring this fall.

Stockbridge

The town is perfect for a fall stroll. The downtown is quaint, contains cozy inns and fireside dining. Don't forget to take advantage of photo opportunities at the town's historic Red Lion Inn. The town is also ideal for a winter visit.

READ MORE: One of America's Best Small Cities for 2025 is in Massachusetts

Lenox

When it comes to culture, Lenox is second to none. With nearby historic venues like Tanglewood and Ventfort Hall, along with boutique shops and historic mansions, you wouldn't want to make a trip to the Berkshires and not include Lenox in your itinerary.

Great Barrington

One of the hippest towns in the Berkshires, Great Barrington contains downtown shops, including coffee shops, bookstores, antique shops, plenty of farm-to-table restaurants, and the historic Cove Bowling Lanes. Great Barrington also has plenty of fall hiking opportunities, including the trails at Monument Mountain Reservation.

Shelburne

The only town on this list that isn't located in Berkshire County, Shelburne, is a fall portrait. The town is home to the beautiful Bridge of Flowers, which was recently renovated, along with glacial potholes and its breathtaking waterfalls. Don't skip this Franklin County town, especially in October.