And all of its charms are nestled in one of the most beautiful natural settings youll ever lay eyes on. Whether you're a local, new in town or just cruising through we've got loads of great tips and events. Stockbridge, Massachusetts is a huge city, and so is the number of ways in which you can have fun here. I was too, which is why I started this 8 things you absolutely cannot miss itinerary series. Guided tours are available at 11 am, 12 pm, 1 pm, and 2 pm. Youll find everything from jewelry and souvenir stores to local chocolate and wine! Explore the city on sightseeing tours, soak up culture at museums and galleries, or choose from the many free things to do. Dont miss the greatest Things to do In Stockbridge, Massachusetts, things to do and iconic destination to visit in Where Can You Find the Best Antiques in Sheffield? There are a few picnic tables near the parking area, but no other facilities. However, there are plenty of places to visit in winter in Massachusetts, particularly its picturesque towns. Visit the town of Stockbridge that is like stepping into a winter scene by Norman Rockwell. The picturesque town was used by Rockwell once lived in the Berkshires and used Stockbridge as inspiration when he painted. Have any questions on Stockbridge Massachusetts or want to share your own favorite things to do in Stockbridge MA? Save 15th Bubbles & Truffles, Wine, Beer Tasting, and Chocolate Extravaganza to your collection. Whether youve got little ones or teenagers to keep entertained, weve rounded up summer holiday activities for all ages to enjoy below. Thats why were suggesting a centrally located, budget-friendly motel. During our most recent visit to Stockbridge, MA, our big goal was to check out the Daffodil and Tulip Festival at Naumkeag (more on that later), so we timed our visit to Stockbridge for mid-May. By the late 19th century it expanded into a 100 guest hotel, and to this day it has still retained its colonial features. This doesnt necessarily mean cheap (if youre on a tight budget, check out our dedicated cheap eats list), but definitely does mean value for money. Save LOUISE BOURGEOIS: DOODLING AND THE UNCONSCIOUS to your collection. One of our favorite summertime getaways in Massachusetts is Cape Cod. Compare prices on Kayak before choosing a snazzy convertible that is perfect for Berkshires living. Theres even a cool teapot collection! Where can I rent skis and snowboards in Stockbridge, MA? If youre looking for a day at the beach, head to Lighthouse Beach in Chatham. Offering an endless number of attractions, museums, historical buildings, and entertainment options. All day ski pass is $20/person Monday-Friday and $50/person Saturday or Sunday. Sat, Jan 28, 5:30 PM. One of the best things to do in Stockbridge MA is to peruse the shops on Main Street. Youll come across secret historical sights, a hidden oasis, epic street art and more seriously Instagrammable spots on this tour around the city centres hidden gems. Stockbridge, Massachusetts seamlessly combines 21st-century modernity with Old World charm and beauty. Packing Lists:Find all the inspiration you need with ourAmazon packing lists. You will be full and happy, promise. Many of the sculptures were created by Turn Park founders, Igor Gomberg and Katya Brezgunova, but many talented artists are represented. In fact, some of the best free things to do in Stockbridge, Massachusetts may already be on your Stockbridge, Massachusetts bucket list! Theres no doubt that New England winters can be dreary and cold, tempting us to stay inside all season. If you are traveling with a dog, choosing the Briarcliff is a no-brainer. Visit Chesterwood in 2022: DetailsChesterwood will be open for the 2022 season on May 5! While the menu changes frequently, you can be sure to find a nice selection of New England dishes, including pecan-crusted rainbow trout, roasted pork tenderloin, or oven-roasted duck. This guide to what to do in Stockbridge, Massachusetts in a day makes for the perfect day exploring Stockbridge, Massachusetts. If you detest dogs or are severely allergic, the Briarcliff might not be the place for you. Treat yourself on famous shopping streets or celebrate special occasions at world-class theatre shows, restaurants and bars. Try our three for all Winter Magic Package, where you can have your choice of ice skating, cross-country skiing, or snowshoeing. It was established in 1934 and features dozens of display areas with an emphasis on plants that thrive in the Northeast. No matter what time it is, theres always something exciting to keep you entertained and out of trouble. Here are Stockbridge, Massachusetts spots that are perfect for afternoon stolls, candid couple pictures and stealing your other halfs kisses even when its bloody freezing. Planning a family getaway or a trip with old friends? Money-saving tip: If you find yourself using the same airline repeatedly (we are huge Southwest fans), consider joining their loyalty program and getting an airline credit card. It would make for a great way to start a longer trip around the Stockbridge, Massachusetts, or to see some of Stockbridge, Massachusettss top sights if you have a few hours stopover in one of Stockbridge, Massachusettss airports. Spending the afternoon at Chesterwood is such an interesting activity if youre looking for what to do in Stockbridge MA. You can even order up an in-room Swedish massage! Price: $20 /person for 2 hours. This little artsy town is big on food, shops, and bookstores, not to mention the Tuck Inn, which is the perfect place to rest after a day of exploring. Jiminy Peak offers night skiing between 3-10pm. Things to Do in Stockbridge Shopping in Stockbridge Best Shopping & Malls in Stockbridge, MA Shopping in Stockbridge Enter dates Filters Shopping Traveler favorites All things to do Category types Attractions Tours Day Trips Concerts & Shows Food & Drink Shopping Shopping Gift & Specialty Shops Art Galleries Traveler rating Canoeing, kayaking, and paddleboarding opportunities near you, Your local trail guide for all ages and skill levels, Local fishing holes, gear advice, and retailers, Discover local campsites, helpful hints, and where to buy gear, Education, permits, regulations and where to hunt in your area, Local archery ranges, tips for beginners, and advice on the proper gear, Get started right with local safety education, training, ranges and retailers, Off-road riding in your area, plus instruction, rentals and dealers. We The Medicine - Healing Our Inner Child 2023. I toured during the Daffodil and Tulip Festival, which is a popular event, but the gardens are just as lovely in the summer and fall. Top 37 Things to do in Stockbridge, Massachusetts, CLICK HERE, Where to stay in Stockbridge, Massachusetts In our opinion, these are the very best small towns in Massachusetts to visit when the temperatures drop. You can explore by location, what's popular, our top picks, free stuff you got this. Please. You may recogine one in particular on your trip to the museum. Monument Mountain Reserve is located directly across the street from the Briarcliff Motel, so get up early and leave your car behind. If you want to sleep in a real bed while immersing yourself in the outdoors, you may want to check out this sweet glamping tent in Richmond. It surprises us that not many people view Stockbridge, Massachusetts as a nighttime city. Sat, Feb 11, 8:00 PM + 11 more events. Skiing. 19. We have the low-down on the best cross-country ski rental shops and retailers in MA. And if you want to extend that getaway, say for a week, or even forever, you will find that all of the cities, towns, and villages in the Berkshires have their own secret spots and amazing highlights. Required fields are marked *. Your email address will not be published. Dont miss the greatest Things to do In Stockbridge, Massachusetts, things to do and iconic destination to visit in Stockbridge, Massachusetts. Secondly, what is there to do? The whole hike took just over an hour, perfect for a pre-breakfast workout. But there are also special exhibitions that change with the seasons, as well as educational programs, and a beautiful 36-acre campus. Despite the bustle, I was able to order my cold brew and food and find a shady outdoor spot to relax. Grab a Drink at the Red Lion Inn. Cant decide which winter activity to try? It's one of our favorite, Speaking of spots that look like a Norman Rockwell painting, Deerfield is a great place to go when you need to get away from it all. Read guide to the most romantic things to do Stockbridge, Massachusetts. There are some incredible food trucks, bars and lots of historical importance that cannot be missed on your trip here. Hancock Shaker Village is designated a National Historic Landmark and was added to the National Register of Historic Places on January 31, 1970. * Mahaiwe Performing Arts Center in Great Barrington. 6 Best Small Towns to Explore on a Trip to the Berkshires. Unique Activities in Stockbridge, Massachusetts. For more places to stay in the Berkshires youcan explore the latest prices here! Leashed dogs are permitted. The Unicorn Theatre and the Fitzpatrick Main Stage are both located in Stockbridge Massachusetts, while there is also the Colonial Theatre in Pittsfield. When it comes to unique, Rockport is a sleepy little seaside town in the winter, but that doesn't mean you should skip it. Points of Interest & Landmarks Observation Decks & Towers 10. WebBoots & Belles Father-Daughter Dance! There's so much to love about the town of, Wellfleet was first settled in the 1650s, so it's brimming with local history. Hancock Shaker Village is a living museum located in Pittsfield, Massachusetts. Here are the best things to do in Stockbridge, Massachusetts. Luckily for you, we know Stockbridge, Massachusetts like the back of our hand, and we actually think that some of the best things to do in the city do actually take place outside. Street Food Area in Stockbridge, Massachusetts. Today, Chesterwood is a historic site of the National Trust for Historic Preservation that is open to the public. Visit our privacy policy to read more. We promise. Well, worry no more Ive written a comprehensive guide to the best areas to stay in Stockbridge, Massachusetts and where to stay in Stockbridge, Massachusetts to help you choose the perfect spot to suit your travels. Read Next: The Best Family-Friendly Museums in the Berkshires. Winter offers sparkling skies and crisp, clean air when winter sports are available and the cultural offerings of the summer are extended although with a less ambitious schedule! 10 Fun Things to do in Lenox MA: Tanglewood, Nature Walks, & More, Planning a Visit to the Berkshires: 10 Step Fun & Easy Travel Guide, Hiking Monument Mountain: Guide to the Best Hike in the Berkshires, Bash Bish Falls: Easy Hike to the Tallest Waterfall in MA, Ramblewild: Our High Flying Trip to the Aerial Adventure Park, 6 Best Small Towns to Explore on a Trip to the Berkshires. But there are plenty of places to explore without spending any money at all. 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