Living in New England, I am very fortunate to have 4 distinct seasons and a variety of drivable vacation destinations. This has been especially relevant for me in the last few years, because I am not supposed to fly due to the tight conditions with so many people and their germs, and the same goes for cruise ships.
One of the great places to which I can drive is the Berkshire Mountain Region of Western Massachusetts. Although it is full of antique shops, outdoor sports opportunities, museums/galleries, and theaters, I have never found it to be congested or tourist-y, the way I might if I traveled to Cape Cod in mid-July. That's something I haven't done in over 12 years, and never want to do again! I try to get to the Berkshires once or twice each summer. Currently, I enjoy staying at the 1896 House in Williamstown. This picture shows the pond that is next to one of the buildings, aptly named "Poolside." There is also a "Brookside" building.
One of the great things about the Berkshires is the quality of the accommodations and activities. Only 2 hours from NY City, these small towns in the hills have long attracted city dwellers who wanted to get away from the heat of summer. It welcomes many cultured visitors who expect certain standards. I have not stayed in one motel, guest house, or B&B that was bad. Of course, The Days Inn is always what it is, but it was the nicest one I've ever been in! And the restaurants are amazing, foods I never would see combined in my local restaurants. I feel like I'm a judge on Top Chef when I'm there!
The Hancock Shaker Village is a great way to spend the day for the entire family! It is famous for its round barn and gardens.
Historically, when the major theater-goers left the cities in the summer, the ballet, symphony, and many theaters would close. They would travel to other, more temperate climates and try out new performances. The Berkshires is one of those Meccas for theater. I have been very lucky to see performances by many well-known actors at a variety of theaters. There is something for everyone, musicals, drama, Shakespeare, children's theater. There are also several great theater camps to cultivate our future thespians. My two favorite theaters are The Berkshire Theater Festival and the Williamstown Theater Festival. Williamstown has a gorgeous new theater, only 3 years old, and the Berkshire is one of the oldest in the country. They rarely publicize their famous performers in advance, making it so much fun to show up to see a play and there is Bebe Neuwirth or Blythe Danner. The Mission House in Stockbridge was built in 1739 and features colonial-era antiques along with amazing heirloom gardens. I must confess that my mother took some holly hock seedpods from the garden. They are growing fabulously along her chimney!
Tanglewood is the summer home of the Boston Pops! What a great night out, picnicking on the lawn and enjoying the music. These aren't ordinary picnics of course! People bring chairs, wine or other beverages, and a repast of some of the fresh fruits from the local road stand, along with meats, cheeses and breads from the great area boutique grocers. The Mount was built by author Edith Wharton in 1902, based on principles she set forth in her influential book, The Decoration of Houses. My niece is such a good sport! Most 5 year olds don't enjoy garden tours, but she was patient with me! During the day there is something for everyone to do. If you are into outdoor activities, there is hiking, biking, hot-air ballooning, and swimming in the local ponds. I am NOT into these activities, so I enjoy the museums, shops, and historic home tours. The largest collection of Norman Rockwell's work is housed at the Norman Rockwell Museum, and the Clark Art Institute has an amazing natural setting for a collection of wall art, sculpture, china, and furniture, as well as being a major center for art research.
Naumkeag is an amazing "cottage" home built in 1885, with a variety of gardens designed by Fletcher Steele. I think it's my favorite place, I could sit in those gardens and read while looking out over the town for days!