The Berkshires: Hilltowns in Summer
The Berkshires have gained a reputation as a haven of sophisticated countryside. With strong support for land preservation and the arts, the small communities in the mountains and their foothills are idyllic retreats. Eighteenth-century homes on rolling farmlands, gentle lakes, a dramatic canyon and a sense of small town peace characterize this lush landscape in western Massachusetts.
DAY ONE
This afternoon, arrive in the small vibrant town of Ashfield, one of the ''hilltown'' communities in the eastern foothills of the Berkshires. Beyond the activity on Main Street, Ashfield is rural, with gentle rolling farmlands and winding roads through the woods. You’ll head for the town center, checking into the Inn at Norton Hill, a graceful 1795 home directly across the street from Elmer's General Store – the hub of local activity.
Meet your guide for an afternoon kayaking trip on Highland Lake, part of the DAR State Forest preserve. You’ll find idyllic swimming beaches and 15 miles of mixed-use trails through northern hardwood-conifer forest. Climb the Goshen fire tower for spectacular views of the Connecticut River Valley and the Berkshires. An optional picnic lunch is available today, or you may choose to stop for lunch in a café before driving to the preserve.
Return to your inn in the late afternoon with some time to relax. We suggest walking across the street to dine at Elmer’s (Friday only), where the rotating menu features two entrees per night, one of which is always vegetarian.
Summer evenings in the Berkshires belong to the arts. Tickets can be arranged for scheduled performances by request for one of several venues including Tanglewood, Jacob’s Pillow Dance Festival and the Williamstown Theater Festival.
Overnight Inn at Norton Hill
DAY TWO
This morning begin your day with breakfast at Elmer’s, where the menu includes a traditional full breakfast as well as more creative pairings with names like, “Mount Saint Elmer’s.”
Meet your guide at 9:00am and set out together for Chesterfield Gorge, a dramatic rock canyon that emerged from the sea bed a half-billion years ago, with 70-foot-high walls carved by glacial action and roaring meltwater. The Gorge has been further formed by centuries of rushing water from the East Branch of the Westfield River.
Hike or bike the dirt road along the shores of the river for up to 10 miles culminating in a half-mile trail along the cliff tops, taking in the breathtaking views of the gorge and river below. Surrounded by a forest of hemlock, ash and oak, the recreation area is home to bears, bobcats, and wild turkeys.
En route, you will stop for a picnic lunch, with time to swim, skip rocks, or just rest.
At trip’s end, visit the Old Creamery in historic Cummington, a small country store with a big vision. Make sure to pick up dessert for the road. Choose from an abundant selection of cookies, bars, sweet breads, and jumbo cupcakes, or an assortment of enticing, beautiful, and delicious cakes, pies and pastry.
This afternoon, meet your guide’s team of sled dogs. Marla BB is a skilled handler and breeder who has participated in the Iditarod race with others and is now putting together her own team of Alaskan huskies. During the spring and summer months activities vary depending on the weather. You will have a chance to interact with young dogs in the “puppy pen,” learn about their training schedule, and when possible, try your hand at dog “cart” rides or dry-land mushing.
This evening, we suggest a walk north on Buckland Road to the Ashfield Lake House for dinner. This casual lakeside restaurant and bar is lively on weekend nights, often featuring live music. Alternatively, head to nearby Shelburne Falls where you’ll find Gypsy Apple Bistro, upscale dining in a hip and elegant atmosphere (reservations recommended).
Overnight Inn at Norton Hill
DAY THREE
After this morning’s breakfast at Elmer’s, check out of the inn and drive to the town of Charlamont, where you’ll meet your guide at the Deerfield River Watershed at 10:00am to begin your whitewater kayaking excursion. This is a basic paddling route with a difficulty level of class I or II. Optional whitewater rafting trips for more advanced paddlers (class III or IV) are available by request.* Your day includes a picnic lunch of delicious sandwiches from the home cooking of Curtis’ Country Store in Charlamont.
Take in the gorgeous scenery as you watch for bald eagles, and exotic ducks swimming or sunning on the rocks along the shore. You’ll travel a little further down the road to Shelburne Falls, crossing The Bridge of Flowers to the pothole dams, an incredible geological wonder. Over 50 glacial potholes are clustered in one of the largest known concentrations of these natural sculptures, ranging in size from 6 inches in diameter to the largest pothole on record at 39 feet across. The stone, in shades of beige, brown, yellow, red, gray, green, black, and white is a mystical sight.
Depart at your leisure, returning home or continuing on to your next Willing Foot destination.
*Additional fees apply.
Detail Page
*Price is subject to change due to date and time of year of booking as well as to currency fluctuation. The price is only an estimate at this time and an accurate costing will be provided when itineraries are chosen and submitted. Prices are based on double/twin occupancy.
Inclusions:
- Accommodation: 2 nights
- All guide services per itinerary
- Kayaking excursion: Half day
- Chesterfield Gorge, Westfield River, and sled dogs: Full day
- Whitewater kayaking (Class 1 & 2): Half day
- Days 2 & 3: Breakfast
- Days 2 & 3: Lunch
Exclusions:
- International and domestic Airfare
- Passport, visa, immigration fees
- Personal items, such as alcoholic beverages and laundry
- Baggage/accident/travel insurance
- Rental car
- Optional whitewater rafting (Class 3 & 4): Additional cost $100
- Gratuities
Please Note:
- We recommend that our clients consult their General Practitioner or Travel Clinic for advice on necessary vaccinations or medicines depending on the region to which they are traveling.
- All guests are strongly advised to take out comprehensive travel insurance covering them for all personal effects, personal accident, medical and emergency travel expenses, cancellation, and curtailment.
- Self-drive passengers renting a car are required to carry a valid international driver's license.




