Berkshires Travel

Picture Yourself in a Norman Rockwell Painting in Stockbridge, MA

Nestled in the heart of the Berkshires the town of Stockbridge, Massachusetts is the quintessential New England town straight out of a Norman Rockwell painting. Literally!

Located about 2.5 hours from both New York and Boston the easiest way to reach the town of Stockbridge is by car although bus is also a possibility.

No matter which way you enter Stockbridge you’ll be greeted by historic buildings, bustling streets, cultural attractions and smiling faces. If you are driving on Route 7 coming from the the town of Lee, park your car and take a peak at the Stockbridge Library. Founded in 1862, the Stockbridge Library, Museum & Archives is one of the oldest libraries in the area holding living history programs, casual literary gatherings, reading, art and receptions.

You’ll be greeted by friendly faces that would gladly help you find everything you need for quiet read on one of the town benches and green parks or a movie night with your family at your cottage. The Historical Room in the library is a museum and research center containing artifacts from town residents, including the original inhabitants, the Mahican Indians. The Library has a lot of interesting events every week and you can find all of them here. One of our all time favorite events that they put together was the Walk Back in Time where the town completely transforms and brings visitors back 150 years ago for a history lesson of it’s best kind.

Continue down the street from the library and check out all the little shops along the way. Grab a bite to eat at the Stockbridge Country Store. The store is a landmark that now holds a small shop as well as a cafe and the food here is delicious. They have the best ice cream in town with a pretty good selection and some unique flavors. The store does get busy sometime so be prepared to wait a few extra minutes for a seat, but it is so worth it. We love treating our littles to an ice cream before lunch and have them eat it on the bistro tables outside while waiting on a table to open up. It has turned into our tradition and it is always something they look forward while visiting in town. As long as they eat their lunch as well!

Right pass the General store you’ll find the Mews. Tucked away in between all the cul-de-sac shops the restaurant is the perfect spot for a quirky and cozy lunch away from the hustle and bustle of the streets outside. The food is as fresh as it gets prepared right there in house and possibly the best you’ve had in a long time. This small restaurant with friendly service and warm atmosphere makes for a tasty experience sure to delight your soul and senses.

And if you are anything like us and like to walk off all the yummy food you didn’t feel guilty enjoying, continue down the road to one of the most famous attractions in town- “The Red Lion Inn“. This iconic landmark was built in 1773 as a tavern and in 1968 bought by Jane Pratt Fitzpatrick when it was threatened to be demolished to build a gas station. They moved their successful mail order business into the building and continue renovations on the Inn. Today Red Lion Inn is a historic landmark and is one of the few American Inns that have operated continuously since before 1800.

The Inn is a marvelous thing to see during each season. Inside it is like a museum, filled with lots of antiques and collectibles but feels intimate and charming. Take a seat on one of the rocking chairs on the front porch with a warm coffee or a glass of wine and open a book and get lost in it or just watch the people passing by and let yourself feel fully the wonderful peace and tranquility of your surroundings.

If you plan your visit to the town of Stockbridge in the beginning of December you’ll witness one of the most spectacular events the town puts on. The Town made famous by Norman Rockwell’s painting of the village during the holidays, becomes a magical New England setting decorated with holiday ornaments and festive lights. Main streets turns just like he saw it and painted it in his famous painting back then. Over 50 antique cars all decorated in Christmas wreaths and ribbons line up in front of Red Lion Inn, a horse drawn carriages offer a tour around Main street and there are even holiday concerts and caroling. Kids are invited to take part in the singing or make a Christmas craft. It is a wonderful time to be in town.

The town had seen it’s fair share of English missionaries that first settled here in 1734 and established it as a mission for the Mahican Indian tribe known as the Stockbridge Indians. The town was officially incorporated in 1739 as Indian town but later taken over by British-American settlers. Later on with the arrival of the railroad in 1893 the village turned into a summer retreat for the wealthy. With more and more prominent people looking to spend time in The Berkshires, Laurel Hill Association took over the old train station and replaced the original wooden structure working to beautify the town and encouraging the growth of tourism.

Designed by architect Frank Waller in the English Gothic Revival style and used by the New York, New Haven, and Hartford Railroad until the early 1960’s the beautiful blue dolomite stone building was used for several commercial ventures, including a night club that almost destroyed it after a kitchen fire in 1965. After the incident the structure was purchased by by Berkshire philanthropists Jane and Jack Fitzpatrick’s High Meadow Foundation in 1997 and restored back to it’s original function as a train station. Finally the Berkshire Scenic Railway Museum took formal control of the historic structure in 2013 and “is planning for the future and intends to use the historic building to install historic, educational exhibits and continue to use the property for occasional special events once tourist train service is restored to the Berkshire Line.” Visitors can find Stockbridge Train Station to the left, right pass Red Lion Inn on Route 7, on the way to Great Barrington.

Across from Red Lion Inn you’ll see the Great War of Rebellion Monument-  A monument to the citizens of Stockbridge, Massachusetts that gave the last full measure of devotion to their country.

Continue straight on Main street pass Red Lion Inn and you’ll find yourself by the Mission House. This historic building, designated in 1968 as a rare surviving example of a colonial mission house, was built between 1739 and 1742 by a Christian missionary to the local Mahicans. The history of the house is astonishing and you can learn more about it here. You can tour the gardens daily or call 413.298.3239 to scheduled a tour.

A little further down the road from the Mission House taking right you”ll find the wooded entrance to Naumkeag. You can either go and visit the house this way or drive up to it.

Naumkeag is a must see in Stockbridge! A short walk from the center of Town this Sanford White Berkshire “cottage” is a delight. The Garden is run by the Trustees of Reservation and for $15 you get a tour of the House and Gardens, worth every penny. This is one of the many “cottages” built by the super wealthy in the Berkshires in the late 1800s through the early 1900s. The building has the original furnishings. The gardens are stunning and peaceful and it look as the owners just finished their tea here and left for a ball.

Miles and miles of stunning views in the most delightful landscape with the gorgeous shingle style house in the background this 44-room “cottage” which served as a summer retreat for three generations of Choates is straight out of a fairy tale. Take a stroll through the beautiful Afternoon Garden, Tree Peony Terrace, Rose Garden, Evergreen Garden and the Chinese Garden before heading inside where you can get close to the Shaker chairs, China and all original arts most from the early 20th century. The Gardens are open: June 4 – June 27
Thursday – Mondays 10AM–5PM (last tour at 3:30PM)
June 27 – September 29
7 Days a week 10AM–5PM (last tour at 3:30PM)

Now head back to your car and to one of the many of the other attraction around Stockbridge. We love spending endless hours by Stockbridge Bowl spending time as a family and watching our kids splash in delight by the water.

Stockbridge Bowl was a huge pull for visitors and locals and in 1946 brought the decision for establishing The Stockbridge Bowl Association which has the mission of protecting and preserving the natural beauty and restoring the ecology of The Great Lake.

The shoreline that extends over approximately six miles is a home to about 400 cottages with a public boat ramp making the lake accessible to all. The Stockbridge Bowl is the largest lake within the town at 1¾ miles length and about ¾ miles width surrounded by the slanted hills of the Taconic Range to the north and west and the Berkshire Hills to the east and awing visitors with marvelous views of Tanglewood to the south. You can get the best views of the Bowl from Olivia’s overlook or enjoy many of the recreational activities on the lake. Take a boat ride, spend a day canoeing while enjoying the surrounding landscape, paddle board or ice fish in the winter. There is something for everyone here.

Plan a visit to  Norman Rockwell Museum, The Berkshire Botanical Gardens, Chesterwood Museum and Tangelwood only a short drive away from the town of Stockbridge open year round and offering tours and events. Check their pages for more information, hours and events.

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