20 Must-Do Things in the Berkshires: Your Ultimate Adventure Guide

Welcome to the Berkshires, where every twist and turn feels like a scene from a postcard! If you’re like me and often find yourself dreaming of the great outdoors (and a little art on the side), this charming region is a breath of fresh air. Picture this: you’re trading the honking horns of NYC for the serene sound of rustling leaves and the delightful hum of a small-town vibe. I’ve made the journey up from the city more times than I can count, and each trip reveals something new. Whether you’re up for a brisk hike, craving some locally sourced eats, or itching to soak in some culture, the Berkshires has it all. So, buckle up, roll down the windows, and let’s dive into the 20 unforgettable experiences that will make your getaway truly special!

1. Hike Monument Mountain

Let’s kick things off with a classic: hiking Monument Mountain. This is not just any hike; it’s like a spiritual awakening for your quads. The views from the top? Stunning. You’ll feel like you’re on top of the world (or at least the Berkshires). Plus, you can brag about it to your friends later—because nothing says “I’m an adventurous soul” like a photo at the summit with that #nofilter hashtag.

2. Visit the Norman Rockwell Museum

After sweating out your inner athlete, it’s time to get cultured. The Norman Rockwell Museum in Stockbridge is like stepping into a time capsule of Americana. His paintings are the perfect mix of nostalgia and humor. Trust me, you’ll leave with a warm feeling in your heart and maybe a slight desire to pick up a paintbrush.

3. Explore Mass MoCA

If you’re more into contemporary art, Mass MoCA is where it’s at. It’s an industrial playground filled with mind-bending installations. Seriously, some of this stuff makes you question your entire existence. Pro tip: don’t forget to check out the roof—it’s an art piece in itself!

4. Chill at Lake Mansfield

Feeling a bit exhausted from all the culture? Head to Lake Mansfield. Pack a picnic, take a nap on the grass, or go for a refreshing swim. There’s something magical about floating in a lake surrounded by mountains. Bonus points if you spot a swan (or a duck—no judgments here).

5. Grab a Bite at The Old Inn on the Green

After a day of adventures, treat yourself to dinner at The Old Inn on the Green. This place is all about farm-to-table goodness, and the cozy, rustic vibe is straight out of a movie. Just don’t be surprised if you find yourself lingering over dessert a bit longer than you intended.

6. Stroll Through Great Barrington

A visit to Great Barrington is a must. The charming downtown area is filled with quirky shops, cafes, and art galleries. Grab a coffee, people-watch, and soak in that small-town vibe. Plus, it’s the perfect spot to buy a ridiculously overpriced candle that you’ll convince yourself you need.

7. Experience Tanglewood

If you’re in town during the summer, Tanglewood is a no-brainer. Pack a picnic and enjoy a concert under the stars. The atmosphere is electric, and you’ll be amazed at how a symphony can make you feel all the feels. Don’t forget your blanket—because no one wants grass stains on their fancy pants.

8. Check Out the Berkshire Botanical Garden

For those who appreciate the beauty of flora (and who doesn’t?), the Berkshire Botanical Garden is a slice of heaven. Wander through the lush gardens and take a moment to breathe in the fragrant blooms. You might even leave with some gardening inspiration—just don’t ask me to help with that; my plants have a habit of perishing.

9. Tour the Chesterwood Museum

Step into the world of sculpture at Chesterwood, the former home of Daniel Chester French, the guy behind the Lincoln statue in D.C. The gardens are gorgeous, and the studio is a real treat. You might just find yourself inspired to create your own masterpiece—or at least snap some cool photos.

10. Go Wine Tasting at Balderdash Cellars

After all that exploring, you deserve a drink. Head to Balderdash Cellars for some delightful wine tasting. The views are breathtaking, and the wine is even better. Pro tip: don’t skip the tasting room’s cheese pairing; your taste buds will thank you.

11. Visit the Clark Art Institute

Art lovers, rejoice! The Clark Art Institute is a stunning blend of art and nature. With its impressive collection and beautiful grounds, it’s the perfect place to spend a leisurely afternoon. Just be careful not to get too lost in thought—before you know it, hours will have flown by.

12. Hike the Appalachian Trail

For the truly adventurous, tackle a section of the Appalachian Trail. Whether you’re an experienced hiker or a novice, there are plenty of trails to choose from. The fresh air and stunning vistas are invigorating. Just remember to bring snacks—because hiking is basically an excuse to eat more, right?

13. Discover the Mahaiwe Performing Arts Center

If you’re in the mood for some entertainment, check out what’s on at the Mahaiwe Performing Arts Center. From live music to films and theater, this historic venue has it all. Plus, you can impress your friends by saying you saw a show in a 1905 theater—because that’s just cool.

14. Explore Beartown State Forest

Nature lovers, this one’s for you. Beartown State Forest offers some of the best hiking and camping in the area. Keep your eyes peeled for wildlife, and don’t forget to take a moment to appreciate the peace and quiet. If you’re lucky, you might even spot a bear (from a safe distance, of course).

15. Savor Sweets at Guido’s Fresh Marketplace

You can’t visit the Berkshires without indulging your sweet tooth at Guido’s Fresh Marketplace. This local gem offers a fantastic selection of goodies, from artisanal chocolates to freshly baked pastries. Warning: you may want to buy one of everything. Trust me; it’s worth it.

16. Attend a Festival or Event

Check the local calendar for festivals and events happening during your visit. Whether it’s a craft fair, music festival, or farmers market, there’s always something fun going on in the Berkshires. It’s a great way to mingle with locals and soak in the community spirit.

17. Take a Scenic Drive

The Berkshires are stunning in every season, so grab your favorite tunes and take a scenic drive. The winding roads and colorful foliage (in autumn, especially) are Instagram gold. Just make sure to stop and take a few pictures along the way—your followers will appreciate it.

18. Enjoy a Relaxing Spa Day

After all those activities, you’ll need some pampering. Treat yourself to a spa day at Canyon Ranch or any of the local spas. Whether you’re into massages, facials, or simply lounging in a hot tub, it’s the perfect way to unwind and recharge.

19. Visit the Arrowhead Museum

Literary enthusiasts should not miss Arrowhead, the former home of author Herman Melville. The museum offers guided tours that give you insight into his life and work. You might leave with a newfound appreciation for “Moby-Dick” (or at least an understanding of why you avoided it in high school).

20. End Your Trip with a Sunset at a Local Lookout

Finally, wrap up your Berkshires adventure by catching a sunset at one of the local lookouts. Whether it’s from a mountain peak or a cozy spot by a lake, there’s something magical about watching the sun dip below the horizon. It’s the perfect way to reflect on your trip and recharge for the chaos of city life ahead. So there you have it — 20 must-do things in the Berkshires that’ll fill your soul with joy and your Instagram feed with envy. Whether you’re hiking mountains, indulging in local cuisine, or soaking up the arts, the Berkshires have something for everyone. So grab your pals (or go solo if that’s more your style) and make some unforgettable memories in this beautiful corner of the world. Happy adventuring!