Crisp air, glowing hillsides, and a slower pace mark the start of autumn in the Berkshires. It is the season for wandering through orchards, taking a scenic drive, and ending the day somewhere warm and cozy.
If you are planning a fall getaway to Lenox, there are plenty of fall activities in the Berkshires to enjoy beyond admiring the foliage. At Hampton Terrace Inn, a historic bed and breakfast in the heart of Lenox, you are perfectly positioned to enjoy the season. From local farms and seasonal festivals to historic homes and scenic roads, here are some of our favorite ways to experience autumn in the Berkshires.
Peak Foliage Secrets & Midweek Getaways
One of the best things about fall in the Berkshires is that the season does not arrive all at once. Changes in elevation mean that foliage can peak at different times throughout the region. Vermont is about 45 minutes north and Connecticut is about 45 minutes south, putting Lenox right in the middle and making it easy to explore different areas as the foliage changes. October is generally a favorite month for leaf peeping, but the exact timing varies from year to year.
And if you have flexibility in your schedule, consider coming during the week. The leaves are just as beautiful on a Tuesday as they are on a Saturday, but you may find fewer crowds and more time to enjoy the places you came to see. Hampton Terrace also offers significant savings on select Monday through Thursday stays during the fall.
After a day spent exploring, you can come back to the inn and settle into one of our fireplace and soaking tubs. There is something especially nice about warming up by the fire after a cool autumn day in the Berkshires.
Iconic Berkshire Orchards, Farms & Spirits
Fall is also one of the best seasons to get a taste of what is grown and made right here in the Berkshires.
For an autumn outing, head to Bartlett Orchards. Apple picking is a classic fall activity here, and you can also stop by for fresh cider and seasonal treats. For locally made cheese, visit Cricket Creek Farm in Williamstown. The working dairy farm produces award-winning cheeses and offers visitors a glimpse into Berkshire farming. Families can head to Ioka Valley Farm in Hancock for a traditional harvest experience. The farm is known for pumpkins, maple products, farm animals, and seasonal activities.
As evening arrives, add a local spirit to the experience at Berkshire Mountain Distillers. Pick up a locally made spirit to enjoy alongside fresh cider, or make it part of an evening spent talking by the fire.
For more ideas, browse the Berkshires orchards and farms directory to discover additional places to visit throughout the region.
Autumn Adventures, Festivals, & Scenic Drives
Some of the best fall days in the Berkshires are the ones without a strict itinerary.
The Lenox Apple Squeeze is a favorite local tradition and a fun way to experience the community during foliage season. You can also visit Naumkeag for its fall and Halloween events and see the historic estate take on a completely different feel as the season changes.
For a slower-paced afternoon, get in the car and follow one of the region’s scenic routes. The Taconic-Mohawk Trail is a classic choice, winding through the northern Berkshires with plenty of opportunities to stop and take in the views. You can also explore the countryside around Lenox along Routes 7, 41, and 183.
Fall is a wonderful time to visit the Berkshires’ museums and historic properties. Explore The Mount in Lenox, spend an afternoon at The Clark in Williamstown, or step back in time at Hancock Shaker Village. If you would rather spend your evening indoors, check the fall schedule at one of the area’s theaters.
If you are planning a visit later in the year, our Holiday Activities in Lenox guide has more ideas for seasonal events and things to do around town.
What Guests Are Saying
“The Hampton Terrace Inn is a charming, quiet, and clean bed-and-breakfast, conveniently located just a 5–10 minute walk from the center of Lenox, with its excellent restaurants and unique shops. The owner-innkeeper and staff are extremely friendly and knowledgeable about the history of the inn and the surrounding Berkshires. Tanglewood is just minutes away as well as other popular Berkshire attractions. As returning guests, we enjoy the Inn and warm atmosphere. The breakfasts are always tasty and exceptionable!! (Great chef) We look forward to returning again next season.” – Barry M., Google Review
Frequently Asked Questions
When is peak foliage in the Berkshires?
Peak foliage typically occurs in October, although the timing changes from year to year. Because the Berkshires include a range of elevations, different areas can reach peak color at different times.
Are attractions open in October?
Yes. Many of the Berkshires’ museums, historic homes, theaters, farms, and other attractions remain open throughout October. Seasonal hours can vary, so it is always a good idea to check individual attractions before heading out.
What are the best couple-friendly fall activities in Lenox?
Couples can spend an afternoon exploring the scenic roads around Lenox, visiting a local orchard, or touring one of the area’s historic homes. Then, head back into town for dinner before settling in for a cozy evening at Hampton Terrace.
Make Hampton Terrace Your Fall Getaway
There is no wrong way to spend a fall day in the Berkshires. Maybe you will spend the morning picking apples, take the long way home through the mountains, and finish the evening with a drink by the fire. Or perhaps you will fill your day with museums and historic homes before returning to Lenox for dinner.
However you choose to experience the season, Hampton Terrace is a welcoming place to come home to. Book your fall getaway and ask about our fireplace and soaking tub rooms and midweek savings.
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