Theres no doubt that New England winters can be dreary and cold, tempting us to stay inside all season. It surprises us that not many people view Stockbridge, Massachusetts as a nighttime city. In a city as big as Stockbridge, Massachusetts, the opportunities for fun dates are pretty much endless. Points of Interest & Landmarks Observation Decks & Towers. 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 Since a visit to the Berkshires is the best way to shake off winter and transition to spring, weve created a complete weekend itinerary for exploring Stockbridge, MA, and beyond. Dont forget you can find tickets to the top attractions, activities, experiences and tours in Stockbridge, Massachusetts here. A visit to Lost Lamb is a huge treat! Posted in: Im not going to hold it against them because their summer cottages have given us regular folk some beautiful spots to enjoy. Sat, Jan 28, 5:30 PM. These include my unmissable highlights visiting and living in the city, with ideas if youre visiting Stockbridge, Massachusetts for the first time, or you can find unusual things to do in Stockbridge, Massachusetts with the family, more things to do in Stockbridge, Massachusetts with toddlers, plus inspiration for a rainy day in Stockbridge, Massachusetts in my other posts. Across the way, youll see the picturesque Chatham Light. I parked in the small public parking lot across the street because the parking area in front of Six Deopt was already full. We use Kayak to compare prices and find deals from dozens of car rental agencies at once. Plenty of these things to do are free or cheap so keeping children happy neednt break the bank. Things to do In Stockbridge, Massachusetts. Let the fun begin! If youve visited Stockbridge, Massachusetts before, or are planning to in the future, then you may already know just how pricey Stockbridge, Massachusetts can be. Price: $38/person Thursday thru Sunday, and includes all three activities and equipment. Your email address will not be published. Thats a huge window! It is open from Thursday to Monday, 10 am to 5 pm. Hours are Wednesday through Sunday, 10 am-4 pm. There's fun for all the family wherever you wander in Stockbridge. Price: $50/person for 1 hour. The Briarcliff Motel is located on a busy stretch of Route 7 between Stockbridge and Great Barrington. Theres plenty of skiing near Stockbridge, MA. You can also be inspired by dance at Jacobs Pillow Dance now open year-round. 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. Give yourself at least an hour to meander the property while planning your own garden. After parking, cross the Goodrich Memorial footbridge to start your walk. Heres our take on some of the best outdoor activities to do in Stockbridge, Massachusetts right now. Here youll find 3 different and unique paths that will take you around and above the Housatonic River. Price: $35/person Monday-Sunday. We pass them on to friends and family after our trip. Dont miss this insiders guide to exploring the city after dark. Spend romantic time with your sweetheart or bonding time with friends and family here in Lenox, MA. 3. Comedy Check out our web story for Stockbridge, MA next! Where to stay in Stockbridge, Massachusetts, Stockbridge, Massachusetts, for a first visit (or even second/third)? The Guthrie Centre & Foundation The Guthrie Center and Foundation runs a library, a bookstore, and a sculpture park. Click Here. For a complete change of pace, why not try horseback riding in the snow? They also serve more wholesome fare, like yogurt with granola, oatmeal, or poached eggs. Skiing and snowshoeing are two favorite things to do in the Berkshires in winter. Explore the city on sightseeing tours, soak up culture at museums and galleries, or choose from the many free things to do. Flights: We always find great flights using Skyscanner and Kayak. You can even order up an in-room Swedish massage! From plays to concerts and even movie premiers, a summer night with the Berkshire Theatre Group is the way to go! Hawks & Reed Ballroom Greenfield, MA. Where can I rent ice skates in Stockbridge? Theres never been a better time to take advantage of the great outdoors and all the things to do in Stockbridge, Massachusetts. Heres a cool bit of literary history as documented by the Trustees, who manage to property: On August 5, 1850, Nathaniel Hawthorne and Herman Melville enjoyed a well-chronicled picnic hike up Monument Mountain. 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! to your collection. Trekking uphill with ones sled is a fair price to pay for the sensational rush from that downhill ride. Try our three for all Winter Magic Package, where you can have your choice of ice skating, cross-country skiing, or snowshoeing. Once Upon a Table is a bistro-style restaurant in downtown Stockbridge, closed Tuesdays and Wednesdays. Be very careful crossing the road, as the cars are pretty speedy here. If you couldnt tell already, there is an abundance of great nature activities in Stockbridge Massachusetts. Hundreds of Frenchs preliminary models and final works are on view in the artists studio, and the woodland walk is also a must-do, with far-reaching views of the Berkshire hills. Consider renting a car in one city and dropping it off in another for an epic road trip! Stockbridge, Massachusetts is a lively city that stays busy almost all hours of the day. Dont worry, even if youre not staying overnight at the Red Lion Inn you can still enjoy it! Whether its a birthday, anniversary, wedding proposal, or simply a ride over the hills into the sunset,a horseback adventurecan make it an experience that will provide a lifetime of memories. The Berkshires are alive and active year-round! Stockbridge, Massachusetts is one of the most expensive cities on the planet, right? Fun VacationCourtyard by Marriott Lenox Just a quick drive from downtown Lenox, this is the perfect spot to relax after a fun day of exploring. We have the low-down on the best cross-country ski rental shops and retailers in MA. I suggest setting aside two to three hours to explore the house and grounds at Chesterwood. OnlyInYourState may earn compensation through affiliate links in this article. Ventfort Hall Gilded Age Mansion, and Naumkeag. Ready for some shopping? Bundle up and spend a day or a weekend exploring one of these charming gems. Jiminy Peak offers night skiing between 3-10pm. If we are planning on hiking, we also purchase a Falcon guide in the Best Easy Day Hikes series.Outdoor Gear: We are REI Co-Op members. From local paths to huge trail systems, find all of the best places to cross-country ski in near Stockbridge, MA. Two are within 15 minutes and the others within 45. There is nothing more exciting or romantic than a getaway to the Berkshires in the winter! Hours of operation are Thursday-Monday from 10 am-4 pm. The stone church was built in 1884 and includes a large number of beautiful stained glass windows. Here are a few ideas! The walking paths are gentle and the scenery bucolic, and the larger-than-life sculptures that dot the landscape seem to have been created to interact with and pay homage to the beautiful Berkshire Hills. Another option: Did you know that were kind of crazy about glamping? Save Comedy @ Bright ideas Brewing! Grab your loved one or best friends, bundle up and come enjoy an incredible winter escape. Whether youre looking for family-friendly activities or would rather sit out the rain in Stockbridge, Massachusettss best bars, weve got it covered (literally). Offering an endless number of attractions, museums, historical buildings, and entertainment options. Small seating areas are abundantly tucked in the trees, so be sure to stop and rest while taking in the art that surrounds you. Packing Lists:Find all the inspiration you need with ourAmazon packing lists. Bousquet Mountain offers a 450 long hill with multi lanes to ride and master as you race to the bottom. Download and/or print it to make planning your trip to the Berkshires easy! Monument Mountain Reserve is right across the road. 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. During your visit, be sure to visit the Blue Steps and grove of white birch trees, the Afternoon Garden, Tree Peony Terrace, Rose Garden, Chinese Garden, and of course, the home, which appears almost exactly as it was left in 1958. Whether youre in Stockbridge, Massachusetts for Valentines Day or just have something to celebrate, heres a list of fun, unique ideas for how to get your romance on while in Stockbridge, Massachusetts with your significant other. Dashing through the snow and sliding through the cool air riding on a sled, toboggan, or tube is an exhilarating way to spend the day. Stockbridge is also home to the Norman Rockwell Museum, the largest collection of paintings by the famous artist. in Stockbridge, Massachusetts , Click Here. Berkshire Botanical Gardens 24 acres are generally wheelchair friendly with paths through many parts of the Garden in addition to manicured lawns throughout many other areas. Saddle up to explore the beautiful trails and views mounted on well-trained horses and accompanied and guided by professional horseman. Historic HotelRed Lion Inn This historic hotel is a landmark in the town of Stockbridge. You can also download an audio tour on your phone to help you navigate and explore. Some restaurants are currently offering pickup only. Not only is this area a haven for creatives authors, painters, poets, and sculptors, but it also draws in lots of people from away, who come to explore the abundant culture and natural beauty and then find that they never want to leave! Or, try another winter activity, such as cross country skiing, skating, or snowshoeing at Canterbury Farm. Western Massachusetts is a four-season destination, and its worthy of a weekend getaway just about anytime. Travel Insurance: Never travel abroad without being covered! Wait, didnt our parents always say that we should never swim after a meal? Dont miss the greatest Things to do In Stockbridge, Massachusetts, things to do and iconic destination to visit in Unfortunately, due to its age, Naumkeag is not ADA compliant, but there is accessible parking in front of the main house, as well as an accessible bathroom. A few other perks of the Briarcliff Motel that are worth mentioning: If you want high luxury or hate dogs, the Briarcliff Motel wont be for you, but if you appreciate budget-friendly, unique lodging and friendly folks, I definitely recommend the Briarcliff. The large-scale art installations were created from felled trees at Chesterwood and harmonized beautifully with the wild surroundings and peaceful landscape. After dinner, head home to the Briarcliff Motel. You might as well start off your trip to town at one of the most iconic places in the Berkshires! See also 27 Best and Fun Things to Do in Greenwood Indiana Address: 9 Glendale Rd, Stockbridge, MA 01262 #7. You would be forgiven for thinking that this was a run-of-the-mill, outdated motel, but several things set the Briarcliff Motel apart from the local competition. Naumkeag is managed by the Trustees for Reservations and features a lovely gilded-age home and a 48-acre property. Follow our daily adventures on Instagram@nothingfamiliar! But there are plenty of places to explore without spending any money at all. And we are surrounded by many winter things to do in the Berkshires! Pre-registration is strongly encouraged, but its possible to get on-site tickets if capacity allows. In fact, the Norman Rockwell Museum is a top attraction! Stockbridge is one of the most charming and beautiful towns to visit in Western Massachusetts! There is a small but lively town center and lots of fun things to do in Stockbridge MA. Come with us as we visit the historic downtown and discover all the best activities, museums, and much more. 1. Explore the Town Center 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. Put on your trendiest bobble hat and take your pick from these top Stockbridge, Massachusetts winter activities. This guide to what to do in Stockbridge, Massachusetts in a day makes for the perfect day exploring Stockbridge, Massachusetts. Actually, thats not entirely true, you can pretty much guarantee that the weather will be entirely unpredictable. Literally, you can spend years here and still not have seen or done anything. He enjoyed a long and successful career as an illustrator and lived in Stockbridge for the last 25 years of his life. This hook-shaped peninsula is infused with stunning scenery, coastal beauty, and small-town Presented by the No Ring Circus to your collection. Searching for the perfect Stockbridge, Massachusetts itinerary? Also, if you happen to visit at certain times of the year you can book ahead and reserve tickets to the popular shows where they transform the grounds. Boots & Belles Father-Daughter Dance! 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. Interest & Landmarks Observation Decks & Towers and includes a large number of beautiful stained glass.. That New England winters can be dreary and cold, tempting us to things to do in stockbridge, ma in winter... Or a weekend exploring one of the most charming and beautiful towns to visit in western Massachusetts one. Winter Magic Package, where you can even order up an in-room Swedish massage enjoy an winter! 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