Summer weekend escapes: The Berkshires

By Former Agent

Summer in New York City is fun, but it’s also very, very hot. When the temperatures rise, the city basically turns into a heat lamp, at which point the only way to cool down is to get out of town. Going to the beach is always a great option, but if you’re looking for something a little different, make like a Real Housewife and head north to beautiful Berkshire County, Massachusetts or, as Manhattan elites call it, the Berkshires.

If you live in New York City, Berkshire County’s greatest blessing is also a bit of a curse: it’s remote. You need a car to get there, but it’s an easy drive that should take under three hours, and once you get there, all that effort is worth it. It’s gorgeous, relaxing, and filled with cultural landmarks you can explore.

Here’s a three-day itinerary for the perfect summer weekend in the Berkshires, from a local (I grew up there, not to brag).

Day 1:

Jump in the car and head out early because traffic could add to your travel time. The fastest and easiest route is usually the Taconic State Parkway. If the traffic isn’t too bad, you should make it to Lenox by lunchtime. I recommend Alta Wine Bar, which has an extensive menu filled with salads, sandwiches and plenty of wine. They even have gluten-free bread they’ll heat up and bring to the table with butter (for me, this is a revelation).

Browse the shops in Lenox’s tiny downtown while you digest, then check out a historic destination like The Mount, Edith Wharton’s house.

Tonight, you’re going to Tanglewood, the famous summer home of the Boston Symphony Orchestra. If you’re lucky (or a good planner) you may be able to catch James Taylor, who frequently performs at the giant outdoor venue. The best (and in my opinion only) way to experience Tanglewood is to pack a picnic and sit on the lawn, so before you go, hop in the car and drive down
Route 7 to nearby Guido’s, a gourmet grocery store where you can get everything you need for the picnic of your dreams: prepared foods, snacks, dessert, wine, etc. (Last summer, we even roasted marshmallows over a candle to make s’mores. It worked well enough!)

image alt

Where to stay depends on your budget. If money is tight, drive to nearby Pittsfield, where you’ll have no trouble finding an affordable hotel. There’s a Hilton Garden Inn, a Best Western and even the Crowne Plaza (where I went to prom!) is reasonably priced. As a bonus, Pittsfield is centrally-located, so no matter where in Berkshire County you’re headed next, you’ll be close.

If, however, you’re looking to splurge, Lenox has several luxury hotels, including Wheatleigh, located in a historic mansion, and Canyon Ranch, an all-inclusive spa and resort. If you can, treat yourself!

Day 2:

Stop by Dottie’s Coffee Lounge on North Street in Pittsfield in the morning. They have great coffee and a traditional breakfast menu so you can fuel up before heading north. Once you’ve eaten, head up Route 7 to Williamstown. The half hour drive is gorgeous, and the town is just as pretty (though I must admit I’m partial — it’s my hometown).

Head to the Clark Art Institute while it’s still early because it’s a small museum and it gets crowded. Their collection is impressive, featuring work from Winslow Homer, George Inness, Edgar Degas and so much more, and the exhibitions are always great. The museum is also housed in a beautiful old building overlooking a (new!) reflecting pool and a hillside, and the view alone is worth the price of entry.

When you’re done wandering around the museum (it won’t take long), walk through town — which doubles as the Williams College campus — until you reach Spring Street. You’ll recognize it right away because it’s the only street with stores and people on it. If you’re hungry again (even if you’re not, you’re on vacation so you should eat), duck into Pappa Charlie’s Deli at the top of the street. You’ll notice each sandwich on the extensive menu is named after a celebrity.

If you have any room left, wander down the street to Lickety Split and get some Purple Cow. It’s black raspberry ice cream with white and dark chocolate chips and it’s the best food in the whole entire world. If you’re too stuffed, that’s OK — you’ll have a few more chances later in the day.

Get back in the car and drive about 15 minutes down Route 2 to the Massachusetts Museum of Contemporary Art (Mass MoCA) in North Adams. Two museums in a day may seem like a lot, but they’re such different experiences, and both are worth seeing. Mass MoCA is housed in an old factory comprised of 26 buildings on 16 acres. There are several galleries and amazing exhibitions, including an impressive Sol Lewitt display that’s been there at least 10 years. They currently have a James Turrell exhibition that’s completely inexplicable but an absolute must-see. Bonus: you have a second opportunity to get Purple Cow (Lickety Split operates the museum’s cafe).

When you’re worn out, head to nearby PUBLIC for dinner, where you can get anything from flatbread to risotto to a burger. If it seems like I’m rushing you from meal to meal, that’s because Berkshire living is all about eating and relaxing. If at any point you have time to kill and want to relax, I recommend sitting in a field for a while. There’s always one around.

Once you’ve eaten, drive back to Williamstown because you’re going to the theater. The renowned Williamstown Theater Festival features Broadway-caliber plays without the hassle of Times Square. No matter which play you end up seeing, you’ll be impressed — and probably see someone famous. This summer, for example, Matthew Broderick is starring in the world premiere of the comedy The Closet.

Day 3:

In the morning, head to Patisserie Lenox for coffee and French pastries. After that, I’ll let you choose your own adventure! Here are the options:

  1. Norman Rockwell Museum
    If you aren’t sick of museums yet, this one is pretty special. Located in Stockbridge, it features a huge collection of work from you guessed it, Normal Rockwell, who lived and worked in the town for much of his life. After touring the museum, drive around to see his illustrations come to life. Grab lunch at the historic Red Lion Inn, then jump in the car and drive back to New York feeling refreshed and renewed!

  2. Naumkeag
    If you are sick of museums, how about touring a mansion on a gorgeous estate instead? The Choate family summer home in Stockbridge features breathtaking views and picturesque gardens, not to mention the mansion itself is pretty nice. Afterward, drive into bustling (it’s all relative) Great Barrington, where you can wander through shops and get lunch at the Barrington Brewery. If you’re not driving, sample a local beer or two before you drive back to New York feeling refreshed and renewed!

  3. Go hiking
    Though I’ve directed you to a lot of cultural landmarks, the thing that really makes Berkshire County special is its natural beauty. It’s hill country, so there are plenty of good hiking trails, all of which offer spectacular views. So before you head back to New York, pick up some snacks at Guido’s and climb a hill or two. For some real exercise, head to Olivia’s Overlook, which is the trailhead for a six mile hike. If you just want to walk a little and see some views, go to Richmond’s Hollow Fields instead before, you guessed it, driving back to New York feeling refreshed and renewed!

  4. Sit in a field. As I said, it’s always an option.

Let us know what you think of Nooklyn Stories by tweeting us @nooklyn, reaching out on Facebook, or finding us on Instagram @nooklyn.stories!

Photo Credits:

1) Photo courtesy
2) Photo courtesy Mary Cella
3) Photo courtesy the Clark Art Institute
4) Photo courtesy Berkshire Natural Resources Council