10 Fun Things to do in Lenox MA On Your First Visit

Lenox Town Center

Lenox Massachusetts is highly regarded as one of the best places to visit in the Berkshires! There are so many fun things to do in Lenox MA, from amazing nature trails to historic New England sites, and upscale restaurants. If you’re wondering what to do in Lenox look no further. We got you covered!

Massachusetts Travel Inspiration 

10 Things to do in Lenox MA

1. Enjoy the Town Center 

All the best things to do in Lenox MA begin in the town center. The cute Massachusetts village has a wide array of shops and restaurants for you to enjoy.

It has a high-end vibe but also feels very local at the same time. While there are so many different things to do in Lenox, make sure you spend some time wandering around the main part town.

6 Best Small Towns to Explore on a Trip to The Berkshires

Lenox Town MA

2. Have a Delicious Meal in Lenox MA

One of the best parts about visiting the town center is the many restaurants and bars to check out. Lenox MA may feel a bit exclusive when you first get here, but there are actually different options for any budget.

Check out the Spanish tapas at Brava, have drinks at the Heritage Tavern, or even grab a pizza from Betty’s. Also, don’t forget to enjoy some ice cream after your meal at the Scoop! Below is a quick breakdown of some of our favorite spots to eat in Lenox Massachusetts. 

  • Haven: Bakery and a great place for breakfast. 
  • Alta: Mediterranean menu and wine bar.
  • Betty’s: Some of the best pizza in the Berkshires!
  • Shots Cafe: Awesome little coffee shop in the center of town. 
  • Brava: Did someone say Tapas?!? 
  • Heritage Tavern: Great spot for drinks and a casual lunch.
  • Firefly: Upscale restaurant with outdoor seating.
  • The Scoop: Delicious ice cream on a hot summer day.

Best Food in The Berkshires

3. Concert at Tanglewood 

Welcome to the summer home of the world-famous Boston Symphony Orchestra! Since the 1930’s people have been flocking to this outdoor concert space to enjoy classical music.

There are other popular musicians that have played here including the likes of James Taylor and Taylor Swift. One of the coolest parts about seeing a show at Tanglewood is that you’re allowed to bring your own food and drinks. We’ve seen some pretty elaborate setups here!

Not only is Tanglewood a great place to see a concert in Lenox MA, but the views around this historic concert hall are spectacular. Know that it’s free to walk around the grounds and take in the mountain views even when there’s no concert going on. 

See All the Upcoming Events at Tanglewood

Tanglewood Lenox MA

4. Weekly Lenox MA Farmers Market 

Located right in front of Ceri Boutique is one of the best things to do in Lenox MA! The weekly market is held every Friday from 2-6pm between the months of June and October.

Here you’ll find everything from fresh produce to snacks, and gorgeous summer flowers. There’s no better way to start your weekend off on a trip to Lenox Massachusetts. 

Things to do in Lenox

5. Stroll Through Kennedy Park

The Berkshires are filled with endless nature trails and outdoor activities that the whole family can enjoy. With that said, Kennedy Park is one of our favorites in Lenox MA!

The park has over 500 acres where you can experience mountain biking, hiking, and even cross-country skiing in the winter. 

Lenox MA Kennedy Park

6. Tour The Mount in Lenox Massachusetts 

The Mount is the historic summer home of famed writer Edith Wharton. Built in 1902, the turn of the century home will give you a look into life in New England over 100 years ago. The Mount is the perfect blend of nature, architecture, and history to see on your trip to Lenox MA.

If possible, we highly recommend taking a self-guided tour of the inside. Check the official website for tour times as it is a popular wedding venue. Either way, it’s still worth visiting to walk the Mount grounds.

The Mount Lenox MA

7. Visit Pleasant Valley Sanctuary

Ready for more fun outdoor things to do in Lenox Massachusetts? Pleasant Valley Wildlife Sanctuary is set among 1,000 acres of unique Berkshire’s nature. The trails are mostly flat which makes for an easy day of walking and hiking.

The dense forest is made up of meadows and wetlands, making it an awesome place to go bird watching in Lenox MA. Also, keep an eye out for the friendly beavers! 

Pleasant Valley Sanctuary Lenox

8. Nature Walk at Parsons Marsh Reserve

If you’re searching for more of what to do in Lenox MA outside, Parsons Marsh Reserve is also worth experiencing. The small walking track is only 1/3 of a mile long and great for all ages.

This Lenox Massachusetts trail eventually turns into a wooden platform that ends at the large pond. Parsons Marsh is another sweet spot for bird watchers, and we have even seen the rare Bald Eagle here.

Things to do in Lenox Massachusetts

9. See a Play at Shakespeare & Company

Shakespeare & Company is a legendary theatre that puts on a diverse range of regular acts. One of the best things to do in Lenox MA is to grab dinner in town then catch a show at Shakespeare & Company after.

They also offer some of the most prestigious acting lessons in New England.

Shakespeare & Company Tickets

Shakespeare and Company Lenox MA

10. See Lenox MA From Olivia’s Overlook 

Oliva’s Overlook is one of the most beautiful views in all of Western Massachusetts. There is a small parking lot that packs up on summer and fall days, so get here early if you want it to yourself.

In addition to the epic views, there are a couple of different short hiking trails as well. We drive by Olivia’s Overlook all the time and rarely pass by without a quick stop!

→ Guide to Olivia’s Overlook: Beautiful View and Fun Hiking Trails

What to do in Lenox MA

More Things to do in Lenox MA

Obviously, there are more than just 10 things to do in Lenox Massachusetts. This is a place with countless outdoor activities, great restaurants, and a fascinating history. 

It’s no wonder Lenox MA is known as one of the best spots in the Berkshires! Use this as a loose guide to find your own hidden gems around town.

Have any questions on this article or want to share your own fun things to do in Lenox MA? Leave us a comment below!

Safe Travels,
Brigitte & Jake

 Where in the world are we? Follow our daily adventures on Instagram @nothingfamiliar

Where To Stay in The Berkshires

Ultra Luxury –Miraval Berkshires Resort & Spa – Take in some luxury in this historic Wyndhurst Mansion turned resort. Enjoy golfing, spa treatments, and views of the beautiful Berkshire countryside. 

Fun Vacation – Courtyard by Marriott Lenox – Just a quick drive from downtown and close to all the best things to do in Lenox Massachusetts. While there are plenty of historic hotels and Airbnb’s in the area, we enjoyed having the modern amenities and swimming pool at the Courtyard by Marriot.

Bed & Breakfast – Chambery Inn – This beautiful bed and breakfast is situated out in the countryside of Lee, but still close enough to walk to local restaurants and shops. You’ll also be just a few miles from attractions such a Tanglewood and Butternut Ski Resort.

Historic Hotel – Red Lion Inn – This historic hotel is a landmark in the town of Stockbridge. Stroll through town which is right at your doorstep, or simply watch the day pass you by while sipping on drinks on the front porch.

For more places to stay in The Berkshires you can explore the latest prices here!


Lenox MA

New England Travel Planning 

 Flights: We always find great flights using Skyscanner and Kayak. This way you can plan your trip around the cheapest and most direct routes.

 Accommodation: Compare multiple sites to get to the best deal such as Booking.com and Agoda! Also, Hostelworld can be your go-to source if you’re traveling on a budget. 

Rental Car: We use Discover Cars when traveling. Consider renting a car in one city and dropping it off in another for an epic road trip! 

Tours: Check out Get Your Guide for hundreds of activities around the country. Book a tour of Fenway Park in Boston, skip the line at the Empire State Building in NYC, or go on a Scenic Boat Tour in Portland Maine! 

 Travel Insurance: Never travel abroad without being covered! We’ve been using SafetyWing for the last few years and they are there when we need them.

 Packing Lists: Find all the inspiration you need with our Amazon packing lists. Including our electronics and camera gear, must-have medical items, and long flight essentials

New England Travel

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