Massachusetts
1. Chatham
The town of Chatham is the quintessential Cape Cod community. It has a charming town center, with the obligatory steepled church and village green (there are even band concerts here on summer evenings). It has a beach and a lighthouse and the streets and sidewalks are crowded with people during the months of June, July and August. The architecture is pure Cape Cod. Come here for a true taste of what Cape Cod has always been.
2. Williamstown
Here is the typical College town, vibrant and alive during all the seasons of the year because of the many young people whose excitement and fun-loving attitude spills over into the community itself. The tiny village has a number of restaurants and shops and even a theater. Walking and bicycle-riding are the two favorite modes of transport.
The buildings of Williams College are classic and well-kept. The university is extremely prestigious and has maintained its excellent reputation for decades.
3. Deerfield
This historic town with its famous boarding school, Deerfield Academy, is a delight to explore on foot. The Victorian architecture recalls an earlier time in our country’s history.
Nearby is the Yankee Candle flagship store, a huge draw with tour groups and other individuals because of the popularity of their products.
Rhode Island
4. Newport
Newport may be a little larger than many of the towns mentioned in this group, but it deserves to be included because of its international reputation as a tourist Mecca. For many years, the America’s Cup was the main draw, but since that event has moved to other locations, Newport has managed to continue to attract crowds through creative marketing and numerous other events.
There are film festivals, jazz festivals, folk music festivals, and boat shows, as well as the old standby attractions, such as, the mansions, vacation homes of the turn-of-the-century rich and famous, like the Breakers and Rosecliff, the Touro Synagogue, the oldest Jewish synagogue in the nation, Cliff Walk, a pleasant stroll along the rugged rocky coastline, Seven Mile Drive, an automobile version of the cliff walk, beaches and other aquatic activities.
Add to it all an attractive waterfront area loaded with shops and restaurants and it becomes clear why this town is most popular tourist area south of Boston.
Connecticut
5. Essex
Essex is a classic, old "yankee" town which has managed to avoid the harshness of modern development while exploiting its quaintness. The town center is compact and pleasant to walk, with a number of shops and restaurants to explore. It is especially attractive at Christmas time when lights and a holiday exuberance enhances the old-town atmosphere.
Perhaps the main attraction in town is the Essex Steam Train, which, in the summer, is expanded to include a riverboat trip up the Connecticut River. During Christmas, the train has Santa Claus in attendance and is very popular with families.
6. Stonington Borough
This tiny village in the souteastern corner of the state has an adorable main street with many shops and several restaurants. It is a hidden gem not far from the Rhode Island line. Stop in at Skipper’s Dock for a meal or a snack — the "mussels carbonara" are to die for.
There are several wineries in the vicinity which offer tasting and sales.
7. Litchfield Hills
This is not a town but a series of towns in the northwestern corner of the state which, together, make a great day trip or weekend getaway from almost anywhere in southern New England or nearby New York. Cornwall, Kent, New Preston, and Litchfield are just a few of the picturesque villages can be explored during a driving tour of the area.
There are covered bridges, waterfalls, and lovely village greens to admire and photograph. The area is extremely popular during the autumn, as a "leaf-peeping" destination and some of the towns have festivals or fairs at that time to take advantage of the additional traffic.
