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A Camino-style walking holiday has come to the US. Here’s what it’s like to walk The High Road.

“The journey begins in Pittsfield

“I prepared for my long walk at Dottie’s Coffee Lounge, an aromatic joint in downtown Pittsfield with artwork on the walls and cheddar scallion scones the size of a baby’s head. The official trailhead for The High Road is at Bousquet Mountain ski resort on the south side of town. (Hiker parking is available at the resort.) The High Road will connect directly to downtown Pittsfield in the years ahead. But in the spirit of walking holidays, I decided to walk 3 miles from Dottie’s to the Bousquet trailhead.

“After stocking up on beef jerky and seasoned nuts at the Berkshire General Store, I warmed up with a lively amble past the traffic on South Street. The storefronts and traffic lights receded and suddenly I was wandering past cottages and leafy estates, following South Mountain Road and Tamarack Road to the foot of Bousquet Mountain. Here a High Road trailhead kiosk beckoned beside the vacant ski lifts.”

New York Times

Ditching the Car and Enjoying the View on a Trip to the Berkshires

“For the first time in 50 years, a passenger train from New York had arrived in Pittsfield, a city of more than 40,000 people that is often overlooked by tourists …”

“As beautiful as I expected” …

“Pittsfield is a walkable, former mill city with a lively music scene and a growing number of bars, coffee shops and restaurants, including Dottie’s Coffee Lounge. … there are several places to stay, including the locally owned Hotel on North, a 19th-century, four-story building with exposed brick walls, high ceilings and spacious rooms.”

A Beautiful Summer in The Berkshires

“It is truly remarkable all that Pittsfield has to offer. The incredible natural surroundings are just a small part of it. The showcase of culture is outstanding. Back in town enjoy the lively restaurant scene and take time to take in some breathtaking shows…”

Taverna Travels

Pittsfield, Massachusetts: A Guide to Your Weekend Getaway

“Nestled smack in the middle of Berkshire County, the city of Pittsfield offers everything you need for a weekend escape from New York City. Whether you’re looking for gourmet farm-to-table dining, boutique hotels, endless hiking trails, or world-class theater, Pittsfield offers it all just a short train right away from NYC. ” 

“The city of Pittsfield has something to offer for any type of traveler. … North St is Pittsfield’s charming main road. You’ll find restaurants, shops. and hotels dotting the picturesque city street. … Pittsfield is a city full of artists, and that talent shines through … Hotel on North is an affordable slice of paradise … One of the best things to do in Pittsfield is enjoy the many hiking trails that fill the city. … There is no shortage of great dining options in Pittsfield.”

TripSavvy Logo

I Rode on Amtrak’s Inaugural Berkshire Flyer Route—Here’s What It Was Like

“Decades in the making, new direct train to Pittsfield creates ultimate vacation weekend.”

“The new route to Pittsfield is an excellent escape for those of us living in New York City without a car. Pittsfield is a great destination for every kind of traveler—from theater lovers to foodies, and especially those who want to spend some time in the great outdoors.”

Times Square Chronicles

Staying In Pittsfield

“There is so much to do in Pittsfield MA.” 

Reviews of District Kitchen and Bar, Methuselah Bar and Lounge, Colonial Theatre, Berkshire Palate, Hotel on North, Hancock Shaker Village, Arrowhead and Herman Melville, Pittsfield State Forest and Berry Pond with Barkshire Camino, Dottie’s and public art.