The Berkshires: Hilltowns in Winter
Winter in the Berkshires means sleigh rides, skiing, skating, and for some, sled-dog mushing and ice fishing. Quiet walks through the small town center in the last of the day’s light and evenings by the fire in one of the region’s iconic 18th-century farm houses complete the picture of a perfect weekend in the snow-white countryside.
DAY ONE
This afternoon, arrive in the small but 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 snow-covered 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 year-round hub of local activity.
Once you have settled in, make the short drive to West Chesterfield where you will meet Marla BB a skilled sled dog handler and breeder who has participated in the Iditarod race with others and is now putting together her own team. Meet the sled dogs, visit the young dogs in the “puppy pen” and check out Marla BB’s innovative eco-cabin.
If you arrive in time for lunch, stop at the Old Creamery Coop, a small country store with a big vision. Choose from their plentiful menu of delicious, carefully selected local, artisanal, specialty foods or the locally-sourced deli. 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.
Later, if you wish, you’ll have time for ice skating on Ashfield Pond, a short walk from your inn.*
This evening, dine at Elmer’s (Friday only), where the rotating menu features two entrees per night, one of which is always vegetarian.
Overnight Inn at Norton Hill
*Ice skate rentals can be arranged by request.
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.”
At 10:00am collect your skis and drive to Notchview Reservation in Windsor, MA - a Trustees of the Reservation Conservation Land. With groomed, extensive trails from beginner to expert, Notchview is the best cross-country skiing site in western Massachusetts. A picnic lunch will be arranged for you today, and can be enjoyed in the base cabin, where you will also find a wood burning stove, hot chocolate, rest rooms, benches, a waxing room, and fellow skiers lunching.*
This afternoon, join Marla BB and her team of Alaskan huskies for an exciting sled ride through the DAR State Forest. This preserve includes more than 1700 acres of land along the Upper and Lower Highland Lakes and 15 miles of mixed-use trails through the northern hardwood-conifer forest. You’ll learn about the world of sled dog racing and have the unique experience of mushing through the Berkshires’ foot hills.
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
*Cross-country ski rentals can be arranged by request.
DAY THREE
After breakfast at Elmer’s this morning, take one last walk through the village of Ashfield before checking out of your inn.
You will meet your guide at 10:00amto set out for a private horse-drawn sleigh ride. Depart from the picturesque town of Worthington for a peaceful ride through the Berkshire foothills. During maple sugaring season (mid-February – mid-April) you have the option of visiting a local sugar house. Break for lunch in the café among the maple trees and view the sugaring process first hand when possible.
This afternoon, before leaving the Berkshires, you may wish to visit the Massachusetts Museum of Contemporary Art (Mass MOCA)* on your own. Opened in 1999, Mass MOCA ranks among the nation’s best museums dedicated to contemporary art. Exhibits include work by many of the most important artists of today—both well known, and emerging—focusing on large-scale and complex installations that are outside the realm of possibility for conventional museums.
Alternatively, downhill skiing or ice fishing can be scheduled by request.
Return home at your leisure, or continue on to your next Willing Foot adventure.
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
- Guide services per itinerary
- Visit to Hilltown Wilderness Adventures
- Horse-drawn sleigh ride
- Cross-country skiing: Half day self-guided
- Mushing: Half day
- Days 2 & 3: Breakfast
- Day 2: Lunch
Exclusions:
- International and domestic Airfare
- Passport, visa, immigration fees
- Personal items, such as alcoholic beverages and laundry
- Baggage/accident/travel insurance
- Ski or ice skate rentals
- Museum entry fees
- Optional sugar house visit
- Optional ice fishing
- Optional downhill skiing
- 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.



