Welcome to Central Massachusetts & the Berkshires

Stretch your quads on hiking trails up Massachusetts' highest mountain and through nature preserves that blanket the surrounding hills. Alternatively, ramble through estate homes of the once famous, listen to world-class musicians from a picnic blanket on a well-manicured lawn, and feast on farm-to-table cuisine at chef-driven restaurants. You could easily spend an entire summer hopscotching the patchwork of wilderness areas, while taking in a dance festival here, an illustrious music series there and summer theater all over the place.

At every turn, you'll come across preppy college towns with shady campuses, bohemian cafes and exceptional art museums. And those lucky enough to be here in autumn will find apples ripe for the picking and hillsides ablaze in brilliant fall foliage.

Top experiences in Central Massachusetts & the Berkshires

Travel guides

Starting at $38.99

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Central Massachusetts & the Berkshires activities

$3498 Multi-day & Extended Tours

All-Inclusive Berkshires Vacation Tour

Enjoy complimentary shuttle service from the Albany International Airport and begin the trip with a welcome lunch at the famed Red Lion Inn where you'll meet your three tour guides and the other guests on the trip. Parking for the week is also available for those driving. You'll kick off the trip with a private tour and performance at Jacob's Pillow, the acclaimed modern dance festival. Following the performance you'll dine at the Old Inn on the Green overlooking the Ted Shawn Theatre. You'll return to the Red Lion Inn for evening entertainment in the Lion's Den and return to your room for the evening. On Monday, you'll enjoy breakfast at the Red Lion Inn before visiting the Norman Rockwell Museum for a private guided tour. Following the tour there will be time to explore the scenic grounds of the museum and enjoy lunch on the patio. In the afternoon, you'll have the option to visit the Berkshire Botanical Gardens or Chesterwood, the home of Daniel Chester French. There will be time to relax at the Birchwood Inn in the evening, where your bags will be waiting for you. You'll dine at a lovely French bistro followed by a performance of the Boston Symphony Orchestra at Tanglewood. On Tuesday, you'll enjoy breakfast at the inn and then visit Edith Wharton's home, "The Mount." You'll take a private guided tour, have time to explore the gardens and enjoy a lunch on the patio overlooking the gardens. In the afternoon you can choose to shop in the quaint Berkshires town of Lenox and visit the many artisan shops or visit the Frelinghuysen Morris Studio for a private guided tour of some of Picasso's works. The evening will include a dinner at an American Bistro followed by a play at the Barrington Stage Company. Accommodations for the night will be at the Birchwood Inn. On Wednesday, you'll enjoy breakfast at the inn and then visit MASS MoCA for a private guided tour of the contemporary art museum. Following the tour there will be time to explore the museum, take a guided hike or enjoy a round of golf. Luggage will be awaiting you at the nearby Porches Inn, where you'll relax before dining at Loom, a brand new restaurant by James Beard-award winning chef Cortney Burns. To cap off the day, you'll have top-notch seats at the Williamstown Theatre Festival's Nikos Stage production.  On Thursday, after breakfast, you'll visit the Clark Art Institute for a private guided tour and time to explore the vast museum grounds on your own. Then you'll take in a matinee of the Williamstown Theatre Festival's mainstage production. After a dinner at Mezze Bistro, you'll enjoy raucous late night cabaret put on by the actors from the theatre festival.  On Friday, you'll enjoy breakfast followed by a private guided tour of the Williams College Museum of Art and time to explore shops in WIlliamstown. You will say goodbyes to the group and be returned to the airport or to you car after a wonderful week!

$40 Food, Wine & Nightlife

Martha's Vineyard Small Group Island Tour from Vineyard Haven

This 3 hour tour (2.5 hour narrated tour and 15-minute stops each in Menemsha and  Cliffs of Aquinnah) will introduce you to our 100 Square mile island by giving you the history both past and present of our six unique towns. You will learn about and see: Oak Bluffs: A Victorian seaside resort that was built around the Methodist campgrounds. The campground is now known for it’s beautiful open-air tabernacle and the 300 plus Victorian gingerbread cottages from the mid 1800’s, that replaced the tents once used for summer revival meetings. The Flying Horse Carousel one of the oldest platforms carousels still in use resides here. Edgartown has a picture book setting with its harbor and waterfront, along with its stately white Greek Revival houses built by whaling captains and carefully maintained. The Old Whaling Church with its six massive columns, the Edgartown Harbor Lighthouse, and the historic Harborview Hotel make Edgartown a museum piece community. The busy harbor town of Vineyard Haven – entry port to Martha’s Vineyard since the mid 1600’s and our year-round port. We will take a drive through the scenic up-Island country-side passing through the historic farming towns of West Tisbury and Chilmark, making a 15 min stop in Menemsha an Idyllic fishing village where you can sample some “clam chowdah or lobstah bisque”. You’ll see the breathtaking multi colored clay cliffs of Aquinnah (Gay Head), with its impressive light house where you will have an opportunity to get out take pictures and stretch your legs. Because the island is so diverse, on your drive you’ll catch glimpses of centuries old stone walls, views to the Atlantic shoreline, grazing livestock, rolling hills and historic homesteads. and will go over the bridge used in the filming of the movie Jaws. Our tour guides are all long time island characters who love sharing their love of the island with you, so sit back and enjoy all our island has to offer when you, come and tour with us.

$50 Cultural & Theme Tours


ItineraryThis is a typical itinerary for this productStop At: Aquinnah Cliffs, Aquinnah, Martha's Vineyard, MassachusettsSee the maestic Clay Cliffs and Gay Head Lighthouse. We spend time here for shopping, eating and sightseeing. Duration: 30 minutesStop At: Martha's Vineyard Camp meeting Association (MVCMA), Oak Bluffs, Martha's Vineyard, MassachusettsLearn all about the Gingerbread Cottages in the Methodist Campgrounds, See the iron Tabernacle and some of its original seats from the 1800s, The Pink House and The home where President Grant gave a speech. Get a feel of what it was like back then by going into the museum and getting up close and personal with the artifacts from long ago.Duration: 30 minutes

$79 Outdoor Activities

Small Group Northern Berkshires Zip Line Canopy Tour

Arrive at our base 15 minutes before your start time to register and get ready.  When you enter the base, guides and base staff will help you register.  You will be asked to sign a waiver of liability (minors will need to sign their own and have a parent/guardian sign it as well) and we will check to ensure that you have proper footwear and clothing.  You will be asked to removed dangling jewelry and to wear your hair in a way that keeps it from being an entanglement hazard. After you've registered, get into your harness and helmet and adjustments will be made to ensure a proper fit.  Then it's up to the practice zip! A short hike from the base, our practice zip gives you a chance to get comfortable with zipping, braking and self-rescue on a short, low zip line.  Once everyone is checked out and able to safely zip, guides will take you up to the vehicles which will transport you to the top of the course.   A 10-minute 4x4 ride brings you half a mile and 500 feet vertically uphill to the start of the course.  A short hike leads to the first take-off platform.  The first zip is slow and short to give you a chance to acclimate flying through and above the trees.  The second zip leads to a spectacular view of the Deerfield River Valley and the Northern Berkshires as you perch over the edge of the ridge on a 100+ year old pine tree.  As you travel down the course, the zips get longer and faster.   A rappel at the end of the top section of the course leads to a water break and a short downhill hike to the start of the next section.  The lower course consists of sky bridges and longer zips that culminate your adventure in the trees. A downhill hike leads back to base where you can share stories and memories of the trip and look at photos of yourself zipping just moments before.

$71 Outdoor Activities

Spend a fun day outdoors on a whitewater river rafting adventure

The Zoar Gap trip meets at our base in Charlemont, Massachusetts at 10:30 a.m (Be sure to check your confirmation email for the exact meeting time of your trip). Please try to be on time, since we must work within the schedule of water releases. You will be required to read and sign a release of liability at this time. All guests will be required to wear a Zoar Outdoor issued PFD (Personal Flotation Device) and helmet. You will also be provided with a paddle. We raft a ten-mile section of class II and III whitewater on the Deerfield River in Northwestern Massachusetts. We put in below the Fife Brook Dam and finish the trip at our base camp in Charlemont, MA. The trip usually takes 6 hours, including registration, transportation to the river, swimming stops, a picnic lunch served on the river, and a slide show of your run through the biggest rapids. You should expect to spend about 3 to 4 hours on the river.This trip comes with a picnic-style lunch, and a spread of chips & salsa, hummus or black bean dip, fresh baked rolls with choices of cold cuts and cheeses, as well as lettuce, tomato, condiments, and dessert and a drink. Lunch on this trip may sometimes be served later in the day due to water release times, weather, or other factors beyond our control. 

$114 Sightseeing Tickets & Passes

Exciting Class III and IV Whitewater Rafting in the Northern Berkshires

ItineraryThis is a typical itinerary for this productStop At: Deerfield River, Charlemont, MassachusettsExperience Class IV rafting excitement close to home on the Deerfield River’s most exciting section, the Monroe Bridge Dryway. Combining the rush of advanced whitewater, the beauty of the northern Berkshires and the camaraderie of a paddling adventure, a Dryway rafting trip will be the highlight of your summer.From Factory Rapid past Dunbar Brook, Dragon’s Tooth and Labyrinth, the rolling whitewater keeps you on your toes while the rugged northern Berkshires provide a backdrop of exceptional natural beauty. We stop for a snack along the river, but after the trip, we return to our basecamp where a hearty, hot barbecue lunch and a slide show of the day’s adventures await.Our skilled guides really make the difference on this maze of rocks, holes and waves. Their expertise and friendly professional attitude help make your day memorable. Rafters ages 14 and up are welcome on all Dryway rafting trips. Participants must be comfortable in the water and able to paddle and work as a team. Participants on this trip may be required to swim aggressively wearing a personal flotation device in rocky, fast whitewater. Duration: 2 hours