The Taconics rise like a wall along the Massachusetts-New York border. Half a dozen roads connect the two states where the range lets down its guard, but otherwise only hikers and black bears pass over a ridgeline that runs from Mount Everett in the south to Berlin Mountain in Petersburg, N.Y., in the north. The trick these days is teaching the bears — and maybe some of the hikers — to observe all of the health and safety precautions necessary during these challenging times dealing with a pandemic in the age of COVID-19. Below we offer you a comprehensive list of destinations in the Western Berkshires, with links to their respective websites to help you research and plan your visits.
Seven Berkshire towns lie along the border: they are (south to north) Mt. Washington, Egremont, Alford, West Stockbridge, Richmond, Hancock, and Williamstown. With the exception of Williamstown, they all play second fiddle to the larger towns immediately east of them — and that is one reason that they have something special to offer the visitor, the second-homeowner, and of course their roughly 13,000 year-round residents.
New Hampshire’s Mt. Washington is well known as the highest peak in the East; the Berkshires’ Mt. Washington is a sparsely settled township on a high plateau below the western slopes of Mount Everett, at 2,602 ft. the highest point in the Southern Berkshires. Much of the land belongs to the Mt. Washington State Forest and the Mount Everett State Reservation. The population was only 167 at last count, but Mt. Washington is home to Arlo Guthrie and James Taylor and other lovers of mountain air and the arts. This is a mountain town with a Cultural Council. There’s also a town hall, a library, a church, and a ball field on Garrett Green in the town center; Sunday softball games bring the community together in the summer months, culminating in the All Town Labor Day Picnic.
Mt. Washington also lays claim to Bash Bish Falls State Park, right near the New York border, the highlight of which is the impressive, two-headed, single-drop falls. Access is easier from the New York end, off Route 22 on Route 344 through Copake Falls. If you’re making that approach, you’ll have the option of parking in New York (at Taconic State Park) and hiking in on a level trail, or passing into Massachusetts and climbing down — and back up — on a well-maintained but steeply stepped slope. Swimming in the large pool at the base of the falls is not permitted (though it happens), but there are rocks for sunbathing, and on a hot day the air is cool and fresh. Many children come to know Mt. Washington by attending YMCA Camp Hi-Rock, founded in 1948; there are both overnight and day sessions during the first half of August. (Please note that the parking lot on the Massachusetts side of Bash Bish Park is temporarily closed this summer to prevent overcrowding.)
The Appalachian Trail passes over the summit of Mount Everett, the windswept dome of which offers panoramic views of New York, Massachusetts and Connecticut. The views from Alander Mountain, reachable from a trail in the Mt. Washington State Forest at the western edge of the Taconic escarpment, are also worth the climb. Or you can simply wander in shady Garrett Garden back in the town center and let yourself get lost in a green labyrinth.
Egremont is one town with two villages, the larger one (South Egremont) located at the junction of Routes 23 and 41, the lesser at a crossroads along Route 71. Both villages are easy to pass through, but 1,225 people are happy to live in this peaceful, rural town. Egremont still has a lot of land under cultivation; the mountains rise only along the border, with Catamount Ski Area straddling the New York-Massachusetts line. Catamount offers the longest Zip Tour in the U.S., and you can make reservations for visits 10 a.m. to 4 p.m. every day but Tuesday. The Arial Adventure Park also has visits available for booking 10 a.m. to 2:30 p.m. Both features are expected to be open until mid-October.
Numerous establishments make Egremont a destination for outsiders. Prospect Lake Park attracts campers of all kinds, including those who pull in with an RV at one of the 140 well-appointed campsites; cabins are also available. Families with children enjoy the lake, and the Park makes a great (and affordable) base for exploring the Berkshires. For fine dining in a warm ambiance, the Old Mill (open for dinner at 5:30 p.m., Tuesday through Sunday, by reservation only, and offering takeout by pre-orders received between 3 and 5 p.m.) has built a faithful following serving inspired American and vegetarian cuisine for more than two decades. The elegant 1786 Egremont Village Inn has only 12 rooms, but each one is light-filled and spacious. The Inn is open this summer, and features contactless check-in. The nearby Egremont Barn, built in 1820, sets a different and more rustic tone, and hosts music and other entertainment. Check out the Barn Burger, reputed to be among the best in the Berkshires. The Barn remains lively during the COVID pandemic, with outdoor seating, live music and takeout, Wednesdays through Sunday starting at 5:30.
If you want to get away from it all, try the Jug End State Reservation and Wildlife Management Area in the southernmost portion of the town; the Jug End Loop Trail offers dreamy, scenic hiking. To outfit yourself in all seasons in a beautiful setting, family-owned Kenver is a former South Egremont stagecoach stopover that has been a destination store for outdoor equipment and apparel since 1959; they rent bikes in the summer, too. Kenver is open in Wednesday through Sunday 12 to 5 p.m.
Some say “ALL-ford,” and some say “AL-ford,” but no one would want to call this town of 500 souls off. It consistently rates among the municipalities with the oldest average-age residents in Massachusetts, and among those with the highest per capita income in the Berkshires. And it has one of the lowest tax rates, too, which may account for its popularity among retirees and second-home owners. It has no police or fire department, no state highways, no commercial development, no apartments, no gas station, and until recently it had no high-speed Internet; now it boasts among the highest speeds in the region.
What it does have are beautiful country roads for biking: the mostly level 9.7-mile Alford Loop runs through farmland and woodland along smooth, lightly trafficked roadways; begin either at the south end at the junction of East Road and Alford Center Road or at the north end over the West Stockbridge line at the junction of West Center Road and Wilson Road. For hikers and strollers, the Alford Springs Trails on Berkshire Natural Resources Council land, open to the public without charge, offer moderate treks; the Mother Loop is 2.4 miles, the Father loop, 4.3. Both have abundant blackberries in season and views up and down the Housatonic Valley. Green River and Alford Brook help keep the landscape verdant, and several farms account for some of the open land. Before you decide to move to Alford, bear in mind that the average price of a single-family dwelling there is upwards of half a million dollars. Visiting picturesque Alford, however, is free.
The Mass Pike passes through the northern part of West Stockbridge — Exit 1. The compact downtown block, bisected by the Williams River, makes a pleasant walk-around. The little-traveled roads in the west part of town pass by fields and farms, while the mountains retreat over the New York line. Click here for a full description of West Stockbridge.
It’s not that there’s no there there, just that there’s no obvious town center. The town offices, the school, and the Post Office are strung along Route 41 as it runs on a north-south axis through town. Richmonders are happy with their low-key, rural paradise, however, complete with two fine apple orchards. The town lies due west of Lenox but seems a world away. It’s popular with weekenders like former Massachusetts Governor Deval Patrick and his wife Diane as well as with families, who appreciate the excellent pre-K through 8th-grade school. The Berkshire Equestrian Center is also located in Richmond; lessons available. For the full equestrian experience, book a stay at the historic Inn at Richmond, part of the riding complex.
The orchards — Hilltop Orchards (open 9 a.m. to 5 p.m. daily) in the western part of town off Route 295, and Bartlett’s Apple Orchard and Farm Store (open 7 a.m. to 5 p.m. Monday through Friday, 8 a.m. to 5 p.m. Saturday and 8 a.m. to 4 p.m. Sunday) in the east — are both thriving, year-round operations and idyllic pick-your-own destinations come September and October. There are two wineries, too: Furnace Brook Winery (under the Hilltop Orchards umbrella and located at the orchard, currently offering DIY wine tastings) and Balderdash Cellars, on Route 41, which makes fine wines from carefully sourced grapes. Balderdash is serving wine and locally produced craft beers at outdoor tables but, by Governor’s orders, only if you purchase food onsite. They’re open Thursday and Friday, 5 to 8 p.m., Saturday 12:30 to 4:30 p.m. and then 5 to 8 p.m., and Sunday 1 to 5 p.m. Reservations required.
One third of the N.Y.-Mass. border belongs to Hancock, but the town is also the narrowest of the Berkshires, only three miles across at its widest point. The northern half is bounded by two mountain ridges, giving the mile-wide valley in between a Shangri-La feeling. Route 43 runs along the western edge of the valley, and if you’re just passing through, you’re likely to miss the town altogether, as the center of settlement lies along a discreetly marked byway that soon rejoins the main route. That makes Hancock’s Main Street the road less traveled, and the small-town peace is palpable for those who make the detour. Don’t miss the Taylor Library if it’s open; it seems the entire town turned out for a panoramic photograph a hundred years ago, and it hangs on the wall.
The southern part of Hancock is still physically divided from the northern half by mountains. Children from the south have to leave the state (and come back again) to get to school. The first-rate elementary school, the low taxes (thanks to the presence of Jiminy Peak), and the small-town feel make Hancock a desirable spot to raise a family. Residents work in Williamstown, Pittsfield, Albany, and at home.
Three attractions might bring you to the town. In the north, along Route 43, lies 500-acre Ioka Valley Farm, now in its 4th generation. The Farm raises beef cattle, but it also has other animals, and some of them are pettable; bring your children or grandchildren. Visitors come from near and far to sample the Farm’s maple syrup, purchase the summer produce, pick pumpkins in October, and select a Christmas tree at year’s end. Uncle Don’s Barnyard at Ioka Valley Farm is open Tuesdays through Saturday, 10 a.m. to 5 p.m. through Labor Day, and then weekends in September and October. Jiminy Peak, which rises on the east side of the valley, is also a four-season enterprise these days, following the trend of climate-change-challenged Berkshire ski areas transitioning into year-round recreational centers. Jiminy Peak’s Adventure Park and Arial Park are open daily 10 a.m. to 6 p.m. until September 7, then weekends and holidays from September 12 through the end of October. Online reservations are highly recommended.
In the town’s southeastern corner along Route 20 sits Hancock Shaker Village, a complex of 22 buildings, fields, and woods amid 750 acres. The Village, founded in the 1780s, is the oldest working farm in the Berkshires and became a living history museum in 1960, preserving and interpreting many aspects of Shaker culture. The practice of communal living by the celibate, pacifist, intensely religious Shakers is reflected in the living quarters that remain today. Although their labor was divided into sisters’ and brothers’ work, a number of the most influential Shaker leaders were women, and gender equality prevailed in the 20 communities the sect founded from Maine to Kentucky. They are most famous for furniture and crafts that combine beautiful design, mechanical invention, and fine workmanship. Many examples are on view at the Village in the very workshops in which they were constructed. Shaker design also produced the ingenious architecture of the 1826 Round Stone Barn and the light-filled Poultry House, now used as an exhibition space. The Village is a favorite with families, and children are invited to observe the heritage-breed sheep and goats. Hancock Shaker Village is open Thursday through Sunday, 10 a.m. to 4 p.m. No advance tickets are necessary for self-guided tours, but guided tours are also available by reservation. Seeds Market Café offers indoor and outdoor dining when the Village is open
Further west on Route 20 begins the 36-mile-long Taconic Crest Trail, which heads north through and across Hancock before entering New York, Williamstown, and Vermont. You’ll pass over Misery Mountain with its ten well-defined summits. If that sounds discouraging, consider that the southernmost is popularly known as Bill’s Lunch. Don’t expect trailside takeout, however.
The town also rates its own page in this magazine, which deals mostly with its cultural, academic, and commercial center. It’s not hard to head for the borders (of New York and Vermont), at least if you don’t mind some climbing. The northwest portion of town is occupied by the Hopkins Memorial Forest, managed by Williams College. There are 15 miles of trails to choose from, including some that head up to the ridgeline and join the Taconic Crest Trail, with views over the Hudson Valley.
If the Housatonic Valley and the Route 7 corridor ever get too crowded for you, take Horace Greeley’s advice: Go West. The border towns of the Berkshires await.