The Berkshires, Massachusetts Tours & Activities in 2026

The Berkshires

From $ 9.99

Behind Bibury’s picturesque stone cottages are hidden histories and fascinating tales waiting to be told. On this self-guided audio tour through the village’s ancient streets, you’ll find traces of the Celtic tribes, Roman settlers, medieval weavers, and even Japanese royalty who have left their mark. Starting and ending in the car park near Bibury Trout Farm, you’ll make your way through the village. You’ll wander past iconic landmarks like Arlington Row – the weavers’ cottages from the 1300s that Henry Ford tried (and failed) to relocate to America. You’ll see St Mary’s Church with its Norman architecture and mysterious sundials, and learn why Emperor Hirohito called his visit to this village “one of the happiest periods” of his life. Along the way, you’ll hear stories passed down through generations.

The Berkshires

From $ 10.92

Using an app on your smartphone, you'll be given nearly 120 objects to find during your scavenger hunt. You'll then wander throughout the downtown area searching for the items. Once you've found the object, you'll send a photo in to score points. Along the way, you will perform challenges for even more points. You'll have 13 categories of objects you can find in this city walk, with each object varying in points depending on the difficulty. Don't worry, you won't be alone. You'll have a remote guide that will be texting you during your game if you need help or have a question. They will also encourage you and give you hints along the way! The objective of the game is to have fun, rank #1 on the leaderboard, and try to get as many points as possible by finding all of the objects!

The Berkshires

From $ 10.92

Add a little bit of flavour into your Brighton trip and join our outdoor yoga class with a view. An experience for both visitors and locals. Practising yoga outside adds a new dimension to your practice! The elements of nature turn every class into a creative and playful experience. Enjoy a friendly atmosphere, meet new people, and feel healthier and more balanced! The classes are fine, even with a little bit of summer rain, but we will cancel in case of heavy rain. You can rebook or get a full refund, if the class is cancelled.

The Berkshires

From $ 20.48

Go behind-the-scenes to discover the secrets of Wedgwood's Made-in-England production, you will explore the story of Jasperware from Josiah Wedgwood I’s early experiments to Wedgwood icons like the Portland Vase.

The Berkshires

From $ 27

Experience the magic of the night sky during the Full Moon Paddle, a guided stand‑up paddleboarding experience under the glow of the full moon in Chelmsford, MA. This peaceful evening paddle offers a unique way to connect with nature as moonlight reflects across the water, creating a calm and unforgettable atmosphere. Led by certified instructors, this beginner‑friendly experience takes place on calm, protected waters and focuses on relaxation, awareness, and enjoying the beauty of the evening. No prior paddleboarding experience is required.

The Berkshires

From $ 27

Experience the serenity and magic of paddling under the moonlight with Full Moon Paddle in Amesbury, Massachusetts. This guided evening paddle invites you to slow down, tune in, and connect with nature as the full moon reflects across calm waters. This unique nighttime experience is equal parts peaceful and awe‑inspiring—perfect for anyone looking to try something new, celebrate the full moon, or simply enjoy a quiet moment on the water with like‑minded adventurers. True to SUP YO’s mission, the paddle emphasizes presence, connection, and exploration, rather than speed or performance.

The Berkshires

From $ 27.3

You will get the chance to paddle board along the famous seven sisters and also the other side tide mills. Our experienced team will ensure you can get up close to the cliffs and take you to stunning parts along the coast which include the famous kitty wake birds and the shark tooth cliff. We have a power rib boat that will ensure you get to the most stunning locations. Having been doing paddle boarding tours here for over 5 years you know you will be in safe hands.

The Berkshires

From $ 29

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!

The Berkshires

From $ 29

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!

The Berkshires

From $ 29

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!

The Berkshires

From $ 34.13

Step into Windsor & Eton’s rich past while visiting three historic pubs full of character and charm. This guided walking tour blends captivating local stories with authentic pub culture, offering a truly unique way to explore the town. At each stop, you’ll have 30–45 minutes to enjoy the atmosphere, mingle with fellow guests, and savour the pubs just as the locals do. Between venues, we’ll take short strolls past iconic landmarks, with your guide sharing fascinating tales you won’t find in a guidebook. What you get: + Local guide bringing Windsor’s history to life + Three pub visits, each with its own story and charm + Time to relax, socialise, and soak in the atmosphere We also offer private tours. Flexible days/timings based on guide availability. Available in Italian, French, German or Swiss German. Perfect for corporate events and birthdays. Note: Drinks & food are not included and are available for purchase at each pub.

The Berkshires

From $ 35.49

The only tour of Chawton guided by an Italian lady who lives in the village. During this one-and-a-half-hour walking tour, you will have the opportunity not only to discover the village that Jane Austen knew and loved and its connection to her life, but also to get a glimpse into what life is like today in an authentic English village based the guide's personal experience as a Chawton resident. This is a perfect day trip from London to a quintessentially English countryside village that offers a perfect blend of history, culture and lifestyle.