Lenox is highly regarded as one of the best places to visit in the Berkshires, and for good reason. There are so many fun things to do in Lenox Massachusetts! This small country town is filled with amazing nature trails, historic New England sights, and upscale restaurants. If you’re looking for what to do in Lenox MA we got you covered!
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Massachusetts Travel Inspiration
- Planning a Visit to the Berkshires: 10 Step Fun & Easy Travel Guide
- 10 Fun Things to do in Lenox MA: Tanglewood, Nature Walks, & More
- 10 Fun Things to Do in Historic Stockbridge MA on Your First Visit
- Hiking Monument Mountain: Guide to the Best Hike in the Berkshires
- Bash Bish Falls: Easy Hike to the Tallest Waterfall in MA
10 Things to do in Lenox MA
1. Enjoy the Town Center
All the most fun things to do in Lenox MA begin in the town center! The cute town has a wide array of shops and restaurants for you to enjoy. It has an upscale vibe but also feels very local and New England at the same time. While there are so many different things to do in Lenox, make sure you spend some time wandering around the town center.
→ Explore more of the Area! 6 Best Small Towns in the Berkshires
2. Grab a Delicious Meal
One of the best parts about visiting the town center is the many restaurants and bars to check out. Lenox MA may feel upscale when you first get here, but there are actually different options for any budget.
Depending on what you’re in the mood for you can have some tapas at Brava, 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.
- 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.
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 also other popular musicians that play 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. Even if you aren’t attending a concert it’s free to walk around the grounds and take in the mountain views.
→ Upcoming Events at Tanglewood
4. Weekly Lenox MA Farmers Market
Located right in front of Ceri Boutique is one of the best things to do in Lenox Massachusetts! 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. If you’re looking for what to do in Lenox MA on a Friday afternoon, there is no better way to start your weekend off.
5. Stroll Through Kennedy Park
The Berkshires are filled with beautiful 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.
6. Tour The Mount
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’s not open every day and is a popular wedding venue. Even if you can’t tour the inside it’s still worth it to visit and walk the Mount grounds.
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!
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 a visit. The small walking track is only 1/3 of a mile long, and great for all ages. The 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!
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 education and some of the most prestigious acting lessons in New England.
→ Shakespeare & Company Tickets
10. Take in the View at 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.
→ Guide to Olivia’s Overlook: Beautiful View and Fun Hiking Trails
Have any questions on Lenox Massachusetts 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!
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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!
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USA Travel Planning
Berkshire Guides: 9 Fall Desserts – Ramblewild – Hancock Shaker Village – Clark Art – Berkshire HorseWorks
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 Sea Cave Kayak Tour in La Jolla California!
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!
