Best Things to Do in the Berkshires - A Foodie Weekend Itinerary

The best part about moving to Boston is being well located to explore more of the Northeast. Don’t get me wrong, I enjoy being in the city itself but I love nothing more than a quick getaway. Within weeks of moving here, I made a bucket list and I’m slowly ticking off destinations. I’ll be honest, I’d never even heard of the Berkshires before Boston but I’m so glad I made a trip to this region in western Massachusetts because I fell head over heels in love. This post covers the best things to do in the Berkshires in a weekend (it’s a great itinerary for foodies).

(This blog post is in collaboration with 1 Berkshire. As always, all opinions are my own.)

Things to do in the Berkshires

Why Visit the Berkshires

There are plenty of things to do in the Berkshires. The area is known for outdoor adventures, like hiking, as well as cultural experiences and some fantastic food. The area makes for a lovely romantic weekend getaway. Plus, it’s truly a great destination all year round.

Where to Stay in the Berkshires

For first timers in the Berkshires, Lenox is a great town to base yourself in and there are plenty of options for accommodations. We stayed at Wheatleigh and it couldn’t have been a more perfect experience. The hotel is located in an 1893 home and overlooks the Berkshire mountains. Nestled in the middle of 22-acres, Wheatleigh is the ultimate sanctuary. If you’re looking for a luxurious experience, trust me this is the place to stay.

The Best Things to Do in the Berkshires

Friday

Afternoon

Drive to Lenox and check into your hotel. Your goal is to get here by late afternoon so you have some time to relax before starting your evening.

Grab a cocktail and a snack at Methuselah. You could easily spend an entire evening here. The rustic vibe coupled with the well balanced cocktails and out of this world mushroom tarts, make it the ideal first stop for your trip.

Looking for the best things to do in the Berkshires? Look no further! Click through for a weekend itinerary that is perfect for a foodie traveler.

Evening

If you’re here during the holiday season (November – through end of December), head to Nightwood at the Mount for an outdoor sound and light experience. We sadly didn’t get to make it here as the show was cancelled due to bad weather.

Finish the evening off with dinner. As we were staying at the Wheatleigh, we enjoyed dinner at one of their two onsite restaurants and spent the rest of the evening relaxing. Other options for dinner include District, John Andrews, Red Lion, and Old Inn on the Green.

Saturday

Morning

Start your day off with breakfast and coffee at your hotel. If you’re staying at the Wheatleigh, enjoy breakfast with stunning views in their main dining room or get room service if you want to be a little pampered.

After breakfast, head to the Norman Rockwell museum, one of the top things to do in the Berkshires. Budget at least an hour to go through the impressive collection. I highly recommend starting your visit downstairs where you can see all of his Post cover illustrations. This is particularly impactful as it illuminates the power of illustration art to shape society. Juxtaposed against the conservative covers, the main floor houses his later art pieces that reflect his values of kindness and social equity.

Afternoon

Post museum, head to Haven Cafe for lunch. There are plenty of plant based options making this an ideal choice for vegans/vegetarians. Every single thing that we tried was mouthwateringly delicious. You’ll find yourself wishing you could eat lunch here every day (I’m honestly still thinking about it…). I highly recommend the veggie burrito, the grilled polenta, the kale salad, the soup of the day, andddd any of their baked goods!

You’ll probably have to roll yourself out of Haven Cafe but we all know it was worth it. Your next stop is Balderdash Cellars to try some wine. You’ll be greeted at the door by two of the cutest dogs who will be ecstatic to see you. I highly recommend doing a wine tasting and then settling in with a glass of wine or two (or really however many you want, it is vacation after all) and enjoying the view.

Next up you have the choice of continuing down the wine train and heading to Hilltop Orchards or moving on to some beer. You’ll find plenty of brewery options in the Berkshires but we opted to drive a little bit to go to Bright Ideas Brewing. The head brewer here used to brew at Wicked Weed in Asheville so we had to give this place a try. Trust me, you won’t be disappointed and it’s well worth the hour drive!

Evening

Head back to your hotel to freshen up and relax a little bit before dinner.

Prepare yourself for a treat because dinner is at Apple Tree Inn in their Ostrich Room. On a cold night, this cozy lounge is exactly the place to be. Start dinner off with ordering some cocktails from the talented bartender, Antonio and then choose some dishes imagined by their James Beard award winning chef. The best part? Enjoy your dinner while listening to live music. While we were there we had the pleasure of listening to two talented artists. We honestly did not want to leave. Such a wonderful way to end your evening.

Sunday

Morning

Cry a little bit that your trip is almost at the end but then perk up because you have some great options for your last few hours.

Get a hike in. Check out a list of trails here. Due to the weather, we didn’t get a chance to check out any of the trails (just something to do when we come back!)

Lunch

Get ready for some of the best pizza of your life at Pizzeria Boema. They even have a ton of vegan options! We went with the roasted cauliflower and the warm white bean antipasto to start and then the tartufo pizza and vegetarian pizza. We finished up with a raspberry lemon drop cake and their vanilla almond decadence cake. If you didn’t cry earlier you may cry here because how can food possibly be this good??

Grab your to go boxes (if you ordered what I did you will certainly have leftovers) and get ready to hit the road. Not ready to go yet and somehow still have room to eat? (Hey, I’m not judging) Check out Berkshire Mountain Bakery or Chocolate Springs.

Need more recommendations? Check out Berkshires.org as the quintessential Berkshire planning tool.

Bottom Line

There are so many wonderful things to do in the Berkshires that it should be a destination on anyone’s bucket list. It serves as an ideal weekend getaway with plenty of outstanding restaurants to satisfy even the pickiest of foodies.