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New York City Road Trip to Lenox

New York City Road Trip to Lenox

For a non-beachy summer escape from the city, the Berkshire Mountains are an easy drive North. Combining cool forest breezes, farm-fresh cuisine and more cultural activities than you could fit into a whole month, the Berkshires can’t be beaten. Add to those lakes, a country and slightly bohemian vibe, and you have the makings of a great road trip. Follow the winding, scenic Taconic Parkway to the heart of the Berkshires: Lenox, Massachusetts.

Fuel Up

Depending on how long you want to drive, you can gas up 77 miles from NYC at the welcoming Taste New York at the Todd Hill Service Station on the Taconic, where you’ll also find outdoor vendors and a locavore indoor market. Seasonal favorites from local farms feature here like cider donuts, wines, brews, pickles and syrup. It’s an incredibly worthy destination for the outdoor Farmer’s Market and an unusual sight at a parkway rest stop. Be sure to sample the wines and bourbons from the Hudson River Valley – they may give you inspo for a road trip within New York State.

The vanilla extract collection at Charles H. Baldwin l
Charles H. Baldwin general store’s extensive vanilla extra collection (©Meryl Pearlstein)

A bit further, before you reach the center of Berkshires’ Lenox-Stockbridge-Lee area, you’ll reach quiet West Stockbridge. The unassuming, charming hamlet rings the Williams River. You can grab a bite at Trúc Orient Express, a staple in the town for 42 years, and the place for authentic Vietnamese cooking. Their Happy Pancake—an original family recipe with pork, shrimp and veggies—is so revered that “Food & Wine” listed it as one of their top 40 recipes of all time. Don’t miss the 182-year-old Charles H. Baldwin & Sons where old-timey Massachusetts goodies like Moxie soda, vanilla extract and licorice strings are sold. Walk off your meal at the nearby TurnPark Art Space or the lush Berkshire Botanical Garden at the West Stockbridge-Stockbridge line.

The Happy Pancake from Truc Orient Express is a family recipe l
The Happy Pancake from Truc Orient Express (Courtesy Truc Orient Express)


When you reach your destination, reserve a dinner table at one of the Berkshire’s lovely farm-to-table restaurants. Choices range from Michelin-starred fine dining with a New England flair to classic New England to boutique-y with one-of-a-kind charm.

Michelin-starred dining awaits at Cafe Boulud at Blantyre l
Outdoor Michelin-starred dining at Cafe Boulud (©Meryl Pearlstein)

Chef Daniel Boulud is esteemed for his stellar cuisine in major metro areas like New York City. What began as a summer residency at Relais & Chateaux’ Blantyre in Lenox proved so popular that Café Boulud is now a permanent restaurant at the Gilded Age resort. Its tasting menus are highlighted by dishes like rack of lamb en persillade, grilled swordfish and filet mignon, and all meals are presented and prepared with the fine touch that you would expect from a Michelin-starred chef. The restaurant’s new Dom Perignon Salon sits in a luxe room just outside Café Boulud’s main dining room or outdoor patio. Reservations are required, and smart casual attire is requested.

The Dom Perignon Champagne salon at Blantyre l
Elegant Dom Perignon Champagne Salon (©Meryl Pearlstein)

For the best brunch in the area, Pleasant and Main in Housatonic is a mashup of a general store and café with both indoor and outdoor seating adeptly blending with the bohemian setting of the Berks. The dining room might confuse you at first – it looks like your grandmother’s home with shelves filled with Depression glass, hats straight out of her closet, and familiar knickknacks all crammed in one exceptional room. Mingled within are tables set for a feast of pancakes, omelets, French toast, home-baked pastries and jams. It’s a difficult choice whether to dine indoors or outdoors in the equally funky patio, replete with fountains, stone walls and antique tables and chairs.

The bohemian dining room at Pleasant and Main l
The dining room at Pleasant and Main (©Meryl Pearlstein)

History lovers can time travel at the ever-popular Red Lion Inn. Widow Bingham’s Tavern, the main dining room and outdoor tables all surround you in a Gilded Age setting where your dining companions could have easily been Norman Rockwell, Arlo Guthrie (“Alice’s Restaurant” was written about a location that formerly stood next door) or Edith Wharton. The menu is traditional New England at its best: turkey dinners with cranberry sauce and sage stuffing, popovers, prime rib and clam chowder. The Tavern has a fun selection of local beers.

The Red Lion Inn is a beloved hotel in the Berkshires l
The Red Lion Inn (©Meryl Pearlstein)


Bring your hiking boots and your yoga mat. The area around Stockbridge is filled with trails overlooking Stockbridge Bowl, and the acclaimed Kripalu Center for Yoga and Health offers a complimentary morning yoga class during Saturday morning rehearsals at Tanglewood. You can also plan for a day at Kripalu: this summer’s day pass is a lovely introduction to the center’s wellness activities, outdoor features and vegetarian cuisine.

Tanglewood is the BSO's summer home l
A rehearsal at Tanglewood (©Meryl Pearlstein)

If you can’t fit a full performance into your schedule, book a ticket for a rehearsal at Tanglewood, the summer home of the Boston Symphony Orchestra in Lenox. You can choose a seat in the shed for an up-close view of these talented musicians or bring your blanket and set it up on the surrounding lawn as most people do. The live music is as glorious as you’ll ever hear, and you can expect a mix of classical pieces with featured soloists along with Tanglewood’s popular artist series. Dance lovers will rejoice that Jacob’s Pillow in Becket is back in action, albeit minus one of their theaters which succumbed to a fire in 2020. Kitted out with new socially distanced bench seating against the surrounding forest and hills backdrop, the Henry J. Leir Outdoor Stage is a magical setting to view important dance companies like Ballet Hispanico from Manhattan.

Outdoor dance performances on the stage at Jacob's Pillow l
Jacob’s Pillow stage (©Meryl Pearlstein)

For improved health and a sense of peace, Edith Wharton built her Berkshires home, The Mount, to escape the winters of Newport, Rhode Island. The author of familiar novels “Ethan Frome” and “The Age of Innocence” modeled the house and gardens in Lenox after her favorite European architectural and design styles. Modest by Berkshire’s standards, Wharton’s “cottage” is noted for its elegance and stature and was recently renovated, happily allowing guests to tour its beautiful rooms once again. Outside, gardens are lavishly designed to seamlessly combine formality with the natural plantings of the area. Permanent and changing art exhibits also grace the grounds. A garden tour is also offered.

Edith Wharton's The Mount and gardens in full bloom l
Edith Wharton’s The Mount (©Meryl Pearlstein)

Also featuring outdoor sculptures, the Norman Rockwell Museum in Stockbridge is the area’s most famous art museum. The beloved Berkshires illustrator created more than 4000 depictions of American life, many of which are displayed in the museum on a rotating basis. The museum’s introductory film, shown on the lower level where walls are filled with Rockwell’s Saturday Evening Post covers, is a must-watch to understand Rockwell’s talent in conveying the nuances of American society and history over five decades.

Self-portrait by Norman Rockwell at the Norman Rockwell Museum l
Self-portrait at the Norman Rockwell Museum (©Meryl Pearlstein)


The Lenox area offers a choice of accommodations from pricey to moderate with most in traditional inns (or bed and breakfasts), some renovated with current amenities, other retaining the patina of times past.

The Red Lion Inn

30 Main Street, Stockbridge, MA,  413.298.5545

The Gateways Inn

51 Walker St., Lenox, MA, 413.637.2532

The Inn at Stockbridge (Note: request a quiet room as the inn sits close to the Mass Pike)

30 East St., Stockbridge, MA 413.298.3337

The living room at The Inn at Stockbridge l
The Inn at Stockbridge (©Meryl Pearlstein)