A Printable, Downloadable, PDF version of this itinerary is available for purchase. Includes Places to Stay in proximity.
ITINERARY AS EXCERPTED FROM KAREN BROWN’S E-BOOK:
A trip to New England should include a drive along the western edge of the region through the states of Connecticut, Massachusetts, and Vermont. Fortunately, Route 7 follows the contours of this western edge almost exactly and is the backbone of this itinerary. The “much more” portion comes in when you cross the Green Mountains to visit the towns of Newfane, Townshend, and West Townshend. If you’re interested in antiques, there is no drive with more “opportunities” waiting than this one. If what appeals to you is the charm of countryside, field, and farm; the rural character of this route will delight you. Pretty, little towns appearing around bends in the road after miles of countryside present farmhouses, stately mansions, and summer cottages-each with its own brand of charm. Plan on being in one of these towns to share the experience of Memorial Day or the Fourth of July; when the schoolchildren parade, the girl and boy scouts march, the high-school band plays, the hardware store mans a float, and the fire engine screams its presence.
Recommended Pacing: Allow five nights to complete this itinerary, four if you do not cross over the Green Mountains but continue up Route 7. Spend the first night in the northwest corner of Connecticut in Norfolk. Then the following day, continue north across the border into Massachusetts, luxuriating in the beauty of the Berkshires. Settle for the night in Stockbridge or Lenox. Continue north to Williamstown, and then into Vermont to overnight in Manchester or Dorset. Cross over the Green Mountains and visit the towns of Newfane, Townshend, and West Townshend. Plan to spend the night in one of these towns where there’s an inn that is certain to appeal to you. On day five, conclude this itinerary either by driving north and east to Woodstock, or to Shelburne with its wonderful museum.
It’s important to realize that the number of miles to be driven during any one of these days is not great-to emphasize the point they are noted below (all approximate):
Norwalk to Norfolk – 80 miles
Norfolk to Stockbridge – 30 miles
Stockbridge to Manchester – 70 miles
Manchester to Townshend – 40 miles
Townshend to Woodstock – 65 miles
Townshend to Shelburne – 160 miles
This itinerary has no prescribed “sightseeing” or “timetable,” rather, it affords the opportunity to “experience” New England. You set the specifics. You can decide to meander along at a leisurely pace-pause in front of the post office and walk through the village; look at the plaque that dates a home; go into the local drug store where, if you are lucky, there will be a row of counter stools to sit and have an ice-cream soda. Wander into the antique stores for the experience of seeing your grandmother’s pitcher or the old kitchen spatula. Buy a postcard to send to a friend, a gift for a loved one, or a memento to take home.
If your trip is focused on fall foliage, there can be no better route to follow than this one, for as the leaves of the trees change from green to red, yellow, and orange, you can follow the line of frost and the magic of a countryside in vivid color.
This is New England at its best. This is not the New England where great events of history shaped the founding of the Colonies, or the New England where you walk the beach and squiggle your toes in the sand, dodging the breaking waves. This is the heart of the New England states: where farmers grew their crops, where school was in one room, where the inns usually had a pub, and where having a meal at the place you slept was customary.
Join Route 7 at its southernmost point in Norwalk, Connecticut. If you have just completed the itinerary that ends in the Connecticut River Valley, it will take no more than two hours to reach Norwalk and to begin the route north. If shopping in an upscale suburban community is what you feel like during the morning, go to New Canaan on Route 106 and visit galleries, antique stores, and other high-end shopping. New Canaan is the home of the Silvermine Guild Of Artists with studios for studying and creating many different forms of art. Every May and June the Guild exhibits works by its members. Taking Route 106 from New Canaan back to Route 7 will put you on the path to Ridgefield, which will be the second detour-and you’ve hardly begun! Ridgefield is only an hour north of New York, but you would never know it from the rural character of this lovely town. Old trees line the streets and front the gracious homes, many of which date back to the 18th and early 19th centuries. Here you will find the Aldrich Museum of Contemporary Art, where changing exhibits display the work of today’s contemporary artists.
Back on Route 7, proceed north through Danbury and above New Milford take Route 202 to Litchfield. With its village green and surrounding homes dating back to the 18th century, there is no prettier town in all of Connecticut. The Litchfield First Congregational Church is an architectural treasure, and if you are traveling here in the autumn, the church framed by the seasonal color of the trees will be one of your most memorable photographs.
If you especially like impressionist art, you might want to consider a detour east from Litchfield to visit a wonderful, private art collection that includes Edgar Degas, Ědouard Manet, Claude Monet and James Whistler. The Hillstead Museum, once a private home and a wonderful example of Colonial Revival architecture, offers a tour that includes a guided visit of 19 intact period rooms filled with art and antiques. Located in the village of Farmington, to reach the Hillstead Museum, travel east from Litchfield on Route 118 which merges with Route 4. (Closed Mondays and holidays, www.hillstead.org, tel: 860-677-4787.)
Return north on Route 63 to South Canaan and Canaan, then drive west on Route 44 to Salisbury, yet another charmer.
Cross into Massachusetts and in the towns of Ashley Falls, Sheffield, and Great Barrington, you find a bounty of antique shops. Referring to a local guide, available in most of these shops in the Route 7 area, will enable you to concentrate on those stores most likely to have the treasure missing from your collection. If you’re not an antique lover, enjoy the towns-stop and wander about, have coffee or a bite to eat at one of the local eateries, and just absorb the charm. Ashley Falls is tiny, Sheffield is mid-size, and Great Barrington tends to be the “papa bear” of these three towns and the convenient center with a hardware store and larger supermarkets.
Just 7 miles north of Great Barrington is Stockbridge, that grand old dame of the Berkshires. Whether you stay here or in one of the surrounding towns matters not, for there is much to do in this area. The village of Stockbridge, with its broad Main Street, lovely old trees, and one beautiful old home after another, is worth a full day. At the top of the list is a visit to the Norman Rockwell Museum, which houses the largest collection of the work of this famous American artist. Many pieces were used on the covers of the Saturday Evening Post and his depictions of everyday life ring true and close to home with any viewer. Smiles are difficult to repress! In a totally different vein is Chesterwood, the estate of Daniel Chester French, the creator of the monument to the Minutemen in Concord, Massachusetts and, more importantly, the sculpture of Abraham Lincoln in Washington, D.C. If you want to enjoy the music of the Boston Symphony Orchestra at the Tanglewood Music Festival, held each summer since the 1930s, then you need to make plans to extend your stay. There are several halls in which these musical events take place, but there is nothing like sitting on the lawn with a picnic supper and a bottle of wine for a relaxing summer evening enjoying beautiful music. This is an experience not to be missed. Also in this area are the Jacob’s Pillow Dance Festival, the South Mountain Concert Festival, and summer theater at the Berkshire Playhouse in Stockbridge. The Williamstown Theater is a little more than 30 miles to the north, also on Route 7.
Head north toward the border of Massachusetts and Vermont. Along the way plan to visit the Hancock Shaker Village, located outside of Pittsfield, and then (one of my all-time favorites) the Sterling and Francine Clark Institute in Williamstown. This treasure, built by its donors in a town far away from urban centers that at the time might be threatened by war, has collections ranging from the Renaissance to the great American painters of the 19th and 20th centuries. There are also displays of furniture and porcelain, and (my particular favorite) a wonderful collection of English and American silver. Do find the time for this visit as it’s an extraordinary one-a major museum in a spectacular countryside setting.
Leaving Williamstown, cross into Vermont and continue on to Old Bennington, a charming village dating back to the 18th century and steeped in Colonial history, which lies 9 miles to the west of the commercial town of Bennington on Route 9. Allow time for the walking tour (maps available at the Chamber of Commerce) including the Old First Church, the Bennington Battle Monument, and the Grandma Moses Schoolhouse, where you can see several paintings of the well-known artist who started painting at the age of 70 and continued painting until she was 101.
As a fan of folk art, I find that the primitive-style paintings of Grandma Moses with their naïve renderings of farm and country life (particularly those in winter) to be extraordinarily charming.
Continuing north on Route 7 brings you into the town of Arlington. If traveling between May and November consider stopping at the Norman Rockwell Exhibit located on Route 7-A. A display of his artistry, particularly the work he completed while he lived here from 1939 to 1953 is on display in the former 19th century church. Of special, sentimental interest, local townspeople who posed as models for the numerous Saturday Evening Post Covers work the exhibit and orchestrate a reunion each May. (Tel: 802-375-6423.)
At this point, from Arlington, take Route 7A towards Manchester, detouring for a short side trip along the scenic Equinox Skyline Drive, a 5½-mile drive to the top of Mount Equinox, the highest point in the Taconic Range. Views from the summit are especially wonderful in the fall when the foliage is at its best. Manchester and Manchester Center have lovely old homes sitting along their main streets. One of these beautiful estates, Hildene, was built by Mary and Abraham Lincoln’s only son to make it to maturity. He fell in love with the area and at the turn of the 20th century, purchased 500 acres and built what he termed his ancestral home. It is possible to tour the home and gardens. Also, an exhibition of our 16th president’s personal artifacts is now on display here and referred to as The Personal Abraham Lincoln.
In Manchester Center, there is now a grand array of brand-name outlet shops. From Manchester Center, follow Route 30 for 8 miles into Dorset, a small village with lovely, white clapboard homes, church, and village green (a favorite of mine). Whether you’re visiting in winter with the town dressed in white, in summer with the fragrance of freshly mown grass in the air and the Dorset Playhouse presenting summer theater, or in fall when frost coats the pumpkins and turns the leaves into magical colors, you’re in for a special treat when you visit Dorset.
Leaving Dorset, you pass through more of the same bucolic countryside-farms and fields, rolling hills and valleys, rushing streams, sturdy stone walls, and towering trees-a photographer’s paradise at any time of the year. Take Route 11 to Londonderry and turn south on Route 100 to Jamaica, West Townshend, Townshend, and on to Newfane. Retrace your steps back to Townshend and head north to Grafton, Chester, and Ludlow. This is a winding and relatively narrow route that will enhance your appreciation of the special, unique qualities of Vermont villages. The Green Mountains are home to some of New England’s oldest and most famous ski areas-many a youngster has learned ski technique here. Each mountain has its own distinctive style of skiing and skiers often will have their favorite. Studying the individual ski area descriptions of elevation, number of trails, degree of difficulty, and overall size should make a decision easier as to which to visit. As always, the mid-week package lift ticket is the most economical way to enjoy skiing on any mountain. Don’t count these areas out at other times of the year-many of them run their ski lifts for visitors in the fall when the foliage can be enjoyed from a unique perspective on high.
From Ludlow, you can easily conclude this itinerary in Woodstock by driving north on Route 100 to West Bridgewater then turning east on Route 4. Ever since the 18th century Woodstock has been a magnet for merchants, professionals, and those who wish to live in a sophisticated community. The homes, of many architectural styles, are a legacy of those prosperous citizens. Today this village is not only the commercial center for this area of Vermont, but also provides upscale shopping in its many stores and galleries.
If you are staying with this itinerary, turn west from Ludlow to Route 7 following it north towards Burlington on Lake Champlain and detouring along the way to visit Mendon, Chittenden, and Goshen before arriving in Shelburne. Be sure to visit the Shelburne Museum with its incredible collection of folk art and displays of the crafts, furnishings, art, and tools used in the early years of the 20th century. The complex consists of 37 buildings on a 45-acre setting that is open from late May to late October. A visit to this museum is all but a must, if you can add this extra day to your itinerary. There is the Circus Parade Building, the Shelburne Railroad Station, the Ticonderoga (a side-wheeler steamship), the Stencil House displaying decorative wall stenciling, the Colchester Reef Lighthouse with its collection of marine art, the Stagecoach Inn, and the Electra Havemeyer Webb Memorial Building with a re-creation of rooms from the Webbs’ Park Avenue apartment. With this small sampling of the contents of the Shelburne Museum, you can see that it would be easy to spend more than one day exploring even a portion of what’s here for your enjoyment. You can overnight either in the Shelburne area or nearby Warren or Waitsfield.
This itinerary ends here, but if your travel time permits, consider continuing to the east and spending time in New Hampshire.