For the 50+ Traveler
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Stockbridge, a picturesque village in the Berkshires of western Massachusetts, is often described as quintessential small-town America. Known for its most famous resident, artist Norman Rockwell, the town welcomes you to walk down Main Street as he painted it and step back in time. Stroll along and explore the boutique stores, art galleries, and specialty food shops; tour exquisite examples of Gilded Age architecture and gardens; and venture just a little way from downtown to find lovely nature preserves and walking paths.

You can drive to Stockbridge from Boston in about 2 hours and from New York City in 3 hours, so this is a wonderful destination for a relaxing getaway. Spending a few days in the Berkshires can help you slow down and take a break from the pace of city life. With the variety of sights and activities in Stockbridge, you will find plenty to explore. Here are some highlights to help you plan your itinerary.

1. Start At The Must-See Norman Rockwell Museum

Want to see where Norman Rockwell lived and worked? The Norman Rockwell Museum in the center of Stockbridge ushers you into the artist’s world. You’ll see the studio where he worked, set up as it was in the 1960s. The last of about 20 studios he worked in, he called it “the best studio yet.”

The museum houses an extensive collection of his work. The Four Freedoms, Girl At Mirror, and The Marriage License, along with more than 360 other paintings, are here. You’ll see some of the covers for The Saturday Evening Post that Rockwell painted from 1916 into the 1960s. As he portrayed life through the World Wars, the Great Depression, civil rights struggles, and on into the Vietnam War era, his goal was not to shy away from the issues but to bring them to life. Sometimes he used humor, but a surprising number of his paintings show life in dark times.

You can download the museum’s app to follow along with the audio tour.

Outside, the museum grounds cover 36 acres. Wander as much as you’d like and take in the views of the Berkshires as well as the gardens. Note the apple trees that Rockwell planted for each of his grandchildren.

The Runaway Cafe serves lunch, or you can bring your own picnic. And if you’re an artist, you are welcome to paint or sketch here. The museum store stocks art kits.

Pro Tip: The usual advice is to allow 2 hours at this studio and museum. I found that I spent quite a long time gazing at these original works of art that I had grown up with; they were like old friends. I’d recommend setting aside an entire morning or afternoon so that you aren’t rushed.

The Berkshire Botanical Garden in Stockbridge.

2. Take Time To Smell The Flowers At The Berkshire Botanical Garden

Stockbridge residents are rightly proud of the Berkshire Botanical Garden, with its 15 acres open to the public. The garden includes 25 display areas of different kinds of flowers and plants. Avid gardeners can click on the What’s In Bloom? section of the website for detailed information about and photos of the current flowers.

From May 1 until Columbus Day, all of the areas are open. If you visit at another time of the year, check the website for seasonal events and classes. The Harvest Festival during October is fun and draws quite a crowd.

The Historic Naumkeag Mansion in Stockbridge.

3. Tour The Historic Naumkeag Mansion And Gardens

The Berkshires served as a summer vacation spot for the wealthy during the Gilded Age. From the late 1800s to about 1900, elaborate summer homes popped up all over the area. Naumkeag was one of these, built by New York attorney Joseph Hodges Choate in 1884. It has a different feel than most, because it was actually a family home.

Instead of venturing here for a six-week vacation, the Choates spent April through November here. Mabel Choate bequeathed Naumkeag to The Trustees of Reservations in 1958, and it has since opened its doors to the public.

The “cottage” boasts 44 rooms and sits on 48 acres overlooking the Housatonic River Valley. Choose from guided or self-guided tours of the house and gardens. Be sure to find the amazing Blue Steps. On a sunny day, wandering through the 10 acres of formal gardens is the perfect way to enjoy the outdoors.

Eat lunch at the Oak Cafe on the grounds, or have a picnic.

If you are in Stockbridge in the fall, check out the Naumkeag Pumpkin Show. This celebration of autumn features more than 1,500 pumpkins as well as fall flowers, and most of them are grown right at Naumkeag.

4. Ride The Train At The Lenox Station Museum

The Lenox Station Museum, just 5 miles from Stockbridge, is both a museum and a train station. Volunteers gave time and money to restore the station to its 1903 glory. Exhibits include displays of historic railroad equipment. Take the Lenox Jitney train ride on the grounds for a feel of olden days. The museum is open on Saturdays from Memorial Day through Labor Day.

If you are looking for a longer train ride in the area, you’re in luck. The Berkshire Scenic Railway Museum, run by the same organization, operates a 10-mile Hoosic Valley train ride from Adams to North Adams and back. Train rides are available on weekends from Memorial Day through Halloween, and there are holiday rides available as well. Drive 40 minutes north of Lenox to Adams on Massachusetts Route 8 to catch the train. The ride is not only fun, but it was also named one of the top 10 foliage train rides in New England by Yankee Magazine. Tickets must be purchased in advance online.

Chesterwood, the summer home of Daniel Chester French.

5. Learn About Sculpture At Chesterwood

Chesterwood was the summer home of the sculptor Daniel Chester French, known for the Lincoln Memorial in Washington, D.C., and the Minute Man statue in Concord, Massachusetts. Tour the home, studio, and gardens of Chesterwood and learn more about sculpture. On display are hundreds of French’s models and final works in bronze and marble. A study gallery of French’s sculptures and paintings recently opened.

After perusing the remarkable art, go for a walk in the garden and woodlands surrounding the home.

The Ice Glen Trail in Stockbridge, Massachusetts.

6. Get Out In Nature On The Walking Trails

Records tell us that Stockbridge was once a rundown village with muddy roads, roaming cows, and brambles and weeds. Then, in 1853, the Laurel Hill Association formed to create and maintain hiking trails. It continues to keep these trails in beautiful condition, and it also oversees nature preserves.

Three recreational trails call to visitors to get out in the fresh air.

Mary V. Flynn Trail

This is an easy walk through the woods along the Housatonic River. The Mary V. Flynn Trail isn’t strenuous, but it’s beautiful. The trail is packed gravel and follows the bed of the old Berkshire Street Railway trolley line. The scenery includes birch trees, pines, and cottonwoods. Cross wooden bridges and make your way to a fern bed to wind up back at the boardwalk where you started.

Laura’s Tower Trail

If you’re up for a bit of a climb, head to Laura’s Tower Trail. Start in a stand of pine and hemlock trees, and then move along an outcropping of boulders. At the summit, a metal tower provides a magnificent view of the Berkshires reaching as far as Mount Greylock to the north. When the weather cooperates, you can see almost 70 miles to the New York Catskill Mountains and 50 miles north to Vermont’s Green Mountains.

Ice Glen Trail

Climb over and around giant boulders set in a glacial ravine at the Ice Glen Trail. Pines and hemlocks line the glen. Ice and snow sometimes survive in the crevices of the rocks even in summer, giving the trail its name.

The front porch of the Red Lion Inn in Stockbridge.

7. Rest In The Rocking Chairs At The Red Lion Inn

The Red Lion Inn on Main Street is not only a hotel but also a charming place to hang out. The front porch is stocked with rocking chairs, so you can sit, sip a cold drink, and look out on the heart of town.

Built in 1773, The Red Lion Inn has been offering food and lodging to guests since the colonial days. Plan for a meal in the main dining room -- breakfast, lunch, or dinner. You’ll be served on antique china and colonial pewter while sitting in the glow of the crystal chandeliers. The food is award winning, and the wine list, with more than 400 selections, is a frequent recipient of Wine Spectator’s Award of Excellence.

If you love the historic ambience and want to lodge at The Red Lion, you can choose from 125 rooms in the inn. Or you might prefer one of the stand-alone cottages on the grounds. One unique guesthouse is a remodeled firehouse from the 1950s. It is featured in Rockwell’s painting The New American LaFrance is Here. Make your reservation early, since this is a celebrity favorite.

Pro Tip: The shop at The Red Lion is an ideal place to pick up souvenirs and gifts. You can knock off your whole list here with items such as Red Lion chowder mugs, gift boxes of jams, or stuffed red lions for the little ones.

One of Norman Rockwell’s premier paintings is of Main Street, Stockbridge, in magical wintertime. The artist spent eight years working on it to get it just right. When you visit and fall in love with Stockbridge, you’ll see that the painting’s charm is no exaggeration. With its mix of genteel ambience, history, fascinating architecture, and formal gardens set against the backdrop of the Berkshires, Stockbridge is truly unforgettable.

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