Snake Loops: Sport Touring East of the Hudson

Above the Amenia Hairpin, this lay-by looks over the New York landscape east of the Hudson River.

Snakes employ astonishing methods of locomotion. Legs? Who needs ’em! Using muscles and scales, snakes hug the landscape as they wind along their way. Roads can be like that, with narrow, winding runs of asphalt that hug each rise and bend.

Snaking asphalt brings joy to this motorcycle rider, and east of the Hudson River there’s a region with plenty of it. This area of small towns, farms and woodlands straddles New York’s border with Connecticut and Massachusetts. The rolling landscape means the roads rarely go straight, and with some route planning it’s easy to avoid population centers. Connecting roads with snake-like curves is the inspiration for this ride.

Roughly in the center of this region is the western Massachusetts town of Great Barrington. It has a picturesque, old-fashioned Main Street neighborhood and interesting options for eats, accommodations and entertainment, so it’s a good base of operations for two routes that begin and end there.

Map of the route taken, by Bill Tipton/

My friend Andrew joins me and we’re up early to take photographs in the best morning light. Andrew points out the Mahaiwe Performing Arts Center on Castle Street. Berkshire County, the westernmost part of Massachusetts, is renowned as an arts region, and this historic venue has been a performance site since 1905. One marquee is lit up and the neon calls to be captured.

Mahaiwe (“muh-HAY-we”) Theater on Castle Street in Great Barrington opened in 1905 as a vaudeville house and has presented arts programming continually ever since. A major renovation was completed in 2005.

On Main Street, at the corner of Taconic Avenue, the sun shines brightly on St. James Place. It was built as an Episcopal church in 1857 and by the late 20th century it had fallen into disrepair. But it was renovated and, in 2017, reopened as an arts center with offices and performance spaces.

Built in 1857 as St. James Episcopal Church, the restored St. James Place is now home to several Berkshire arts organizations.

Just south of downtown, we bear right onto Massachusetts State Route 23/41. After a quarter-mile on the left, in a green space next to Silver Street, we find the Newsboy Statue. In 1895, William L. Brown, who was a town resident and part owner of the original New York Daily News, presented it to the people of Great Barrington. I was a paperboy, so it feels right to stop and pay my respects.

The Newsboy Statue pays homage to young entrepreneurs (your humble scribe among them) who spread the news.

When 23 goes right, we stay left on 41 then make a quick right onto Mount Washington Road. It can be hard to find the signs that point the way to Bash Bish Falls State Park, but it’s worth the effort. Turn right onto Cross Road, right onto West Street and left onto Falls Road to the park. Bash Bish Falls is the highest single-drop waterfall in Massachusetts and a short walk from the parking area.

Bash Bish Falls is the highest single-drop waterfall in Massachusetts.

Continuing west lands us in New York, the first of many “border crossings” we’ll be making. We turn left at New York State Route 22, which will make several short appearances throughout our route, then start looking for Under Mountain Road. At U.S. Route 44, we go right and when we reach McGhee Hill Road, begin to meander through sparsely populated areas along serpentine roads.

We curve around Hunns Lake, then in Bangall turn hard left onto Bangall-Amenia Road. A ways on we merge back onto U.S. 44 and pull into the scenic overlook to survey the landscape from a standstill. Just below the overlook — and waiting when we hop back on the bikes — is the Amenia Hairpin, a delightful and downward sloping left curve. Farther along, Halls Corners Road and Chestnut Ridge Road keep us smiling.

Sometimes, snake roads appear to have their own scales.

By the Union Vale Fire House, a right on Clove Road has us winding south and a bit west. U.S. Route 9 eases us to Philipstown, then we turn left onto State Route 301 through Fahnestock State Park. The area ahead is known to local curve-loving riders, and we spot several enjoying it with a mechanical symphony from their bikes’ exhaust.

Back underway we’re on Gipsy Trail Road and County Road 41 to Farmers Mills. Haviland Hollow Road crosses into Connecticut. We wrap around Squantz Pond State Park and back into New York, then roll north through Pawling and Wingdale. At Dog Tail Corners Road we wag left and soon we’re in Connecticut again, crossing Bulls Bridge over the Housatonic River and turning north onto a gently winding stretch of U.S. Route 7 that parallels the river. The quaint village of Kent is a good place for a break, but we make our stop just beyond at Kent Falls State Park to see another great waterfall.

A few miles north is Lime Rock, home to the Lime Rock Park racing circuit. Actor and philanthropist Paul Newman spent a lot of time here, shunning the spotlight, making friends and honing skills that would lead him to the Sports Car Club of America national title (as an amateur) in 1976 and a second place finish with his team at the 24 Hours of Le Mans in 1979. Lime Rock Road goes right past the track, which is quiet today.

Old movie houses like Quirino’s Crandell Theater in Chatham, New York, offer an alternative to the Cineplex.

A right on Connecticut State Route 41 begins the return stretch north into Massachusetts and we arrive back in Great Barrington, leaving 221 snaking miles behind us. I notice that the First Congregational Church, which was in shadow this morning, is now basking in afternoon sun. Built in 1883 from locally-sourced limestone, it’s listed in the U.S. National Register of Historic Places.

Unlike early this morning, Great Barrington’s old-fashioned Main Street neighborhood is bustling now. There are interesting places to eat, shop, explore and spend the night. U.S. Route 7 just north of downtown resembles Anytown, USA, with additional options for accommodations, restaurants and stores, plus a microbrewery.

On such a calm, fair morning, we’re surprised by the absence of pilots at Koladza Airport in Great Barrington.

It’s another early start for day two and another easy roll down Main Street to Massachusetts State Route 23, then right onto State Route 71 and into New York before shooting briefly south onto New York State Route 22 and turning right onto County Road 21. In much of New York, numbered county roads are the roads less traveled, and in this region they embrace the rolling hills and keep me smiling. Sight distances are typically short and forest critters could emerge from anywhere, so I dial up my Spidey senses.

We like that creative use of an inverted curve sign, but wish it was pointing to breakfast.

Crow Hill Road and State Route 203 lead us to Chatham and another still-sleeping downtown. There’s no place open for breakfast yet so we continue to Old Chatham, but the Country Store hasn’t opened either.

My bike’s long shadow reveals how early it is…still too early for breakfast!

County Road 13 snakes through East Nassau and Stephentown, then we curl back west on County Road 16 toward Nassau. A right on Rabie Road curves toward West Sand Lake, then Route 351 goes to Poestenkill and Plank Road goes to Berlin. At State Route 22 we turn north to Petersburg then slither east up Taconic Trail (State Route 2). At the top of the ridge we cross into Massachusetts and wind back down to Williamstown.

Massachusetts State Route 2 cuts through the picturesque campus of Williams College. In front of the Museum of Art, we stop to look at several sets of large, disembodied eyes, sculpted in bronze. I ride my bike onto the sidewalk to set up a photo, and even though no one is around I get the feeling I’m being watched.

“Eyes” by Louise Bourgeios, standing watch next to Goodrich Hall at Williams College.

A short ways on, we turn right onto Luce Road toward Notch Road and the Scenic Byway to the summit of Mount Greylock. On a map, this narrow, 7-mile, seasonal jewel resembles a sidewinder, with successive climbing hairpins. We keep up the revs and power through, while staying alert for trail hikers crossing the road.

From a left at the T, Summit Road rises to the highest point in the Commonwealth of Massachusetts (3,491 feet). Reaching skyward another 92 feet is the Massachusetts Veterans War Memorial, a lighted beacon atop a granite tower, which was completed in 1932 and rededicated in 2017 after a two-year renovation. On a clear day we’d see nearly 100 miles over western Massachusetts, southern Vermont and eastern New York, but today we’re in the clouds.

The Massachusetts Veterans War Memorial rises 92 feet above the summit of Mount Greylock, the highest point in the Commonwealth (3,491 feet).

Also near the summit is Bascom Lodge, built in the 1930s by the Civilian Conservation Corps. Out front I talk with a young couple who are “thru-hikers,” completing all 2,190 miles of the Appalachian Trail, which runs through here. They started in Georgia a few months ago and have a few more weeks to reach the end in Maine. What’s their hike been like so far? “It’s sure a good way to get to know someone,” the young man replies, eliciting a steely gaze and raised eyebrows from his companion.

Back down the mountain, Rockwell Road rewards us with more twisties and hairpins. At the bottom, a right on U.S. 7 and a sharp left on State Route 43 soon has us back into New York and more curvy county roads through Stephentown, East Chatham and Austerlitz. A short run north on New York State Route 22 and then east on State Route 102 returns us to Massachusetts.

Andrew circles (over and over) before Tracy Memorial Village Hall (c. 1913) in Chatham, New York.

Rolling through the village of Stockbridge seems to transport us into a Norman Rockwell painting, and there’s a reason for that. Norman Rockwell lived here, and his experience inspired his iconic scenes of 20th century American life. Fans of his work can go one mile south on Massachusetts State Route 183 to the Norman Rockwell Museum.

State Route 102 continues along the Housatonic River toward Lee and U.S. Route 20, where most vehicles (thankfully) turn into the outlet mall. We continue onto the best stretch of U.S. 20 in Massachusetts, Jacob’s Ladder Trail. The alternating downhill curves going into Chester are downright danceable on a motorcycle, and mellower curves continue all the way to Russell. There, a right on Blandford Stage Road takes the less traveled leg over to State Route 23.

Turning west, Route 23 twists and curls back to Great Barrington, all the way hugging asphalt undulations in that most enjoyable manner: like a snake.

West Branch Reservoir Causeway in Carmel, New York, is the southernmost point in our southern loop.


  1. Great article. I’m familiar with many of the landmarks mentioned. The article and pictures make me want to visit some of the others. Thanks for sharing.

  2. Lovely ride, thanks. I’m thankful that you didn’t cover the best bike road in the area 😉 – secrets must be kept to keep out the riff-raff!! 😀 Hope you discover it (but please, keep it on the down-low!)

  3. Used to live in Carmel when it was a nice little inexpensive place.

    After the WTC attack, a lot of City losers moved there and screwed things up….like the Cost of Living and the culture.

  4. Hi, new subscriber and trying to prepare my around the U.S. ride plans. What I have noticed is that I haven’t found calendar dates for the rides. I’d hate to start this one out too early or late reference typical weather. Even a general “we headed of the second week of September…” in the article would help.


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