One of my favorite things about living in New England is the close proximity of everything. Boston is the epicenter of New England and the perfect home base for exploring all of the charming towns in the region – both big and small. While there are truly countless destinations in the area – best visited seasonally – to choose from, I have been checking them off, one by one, over the past five years. Most of these places are under 3 hours so you have the option to fly, drive or train to them. They are each unique in their own way.
New York City is one of my favorite places in the world to visit and living less than four hours away is a total treat! NYC is great year round, which makes it particularly special. While I love jogging through Central Park in Spring and hitting the rooftop bars in Summer, I also really enjoy throwing on a light jacket in fall and feeling a crispness in the air. Then NYC around the holidays may be my favorite time, as the decorations are up and the music is playing. We go every year for my birthday (in December) and enjoy shopping, dining out and catching a Broadway show. New York is always a good idea.
Saratoga Springs (summer, specifically track season)
Speaking of New York, Saratoga Springs is an incredibly charming city in upstate New York, a mere 3 hours west of Boston. This town thrives during horse racing season, which is late July – early September. The streets are lined with flowers, there is live music every night and people get really dressed up to spend a day at the track. In fact, we love Saratoga so much that we got married there on opening weekend of track season. Such a hidden gem of New York!
Martha’s Vineyard (summer)
A hop, skip and jump away from Boston (and accessible to NY, RI, CT as well), Martha’s Vineyard is a relaxing haven. The island itself is pretty spread out so certain areas feel much more remote than others. If you’re looking for a lot of activities, restaurants and shops then I recommend Edgartown, Oak Bluffs or Vineyard Haven. If you want more remote, less crowded beaches (with views like this), then Chilmark or Aquinnah are a better idea for you. Wherever you decide to stay, I can guarantee that you will take in some beautiful beaches, eat delicious fresh seafood and leave feeling rejuvenated.
Newport (summer, preferably on a boat)
A refreshing alternative to Cape Cod, Newport is an easy 2 hour drive from Boston. Home to the mega-mansions that you will find along the Cliff Walk, Newport has a ritzy-meets-coastal appeal which I love. The site seeing and coastal walks will leave you breathless with the views. The downtown itself is darling, filled with great restaurants (think oysters + lobster rolls), cute shops and family-run stores. My favorite way to visit Newport is by boat – we like to spend the day on the boat, swimming and playing, and then dock in town for dinner by the harbor. Oh, and we can’t forget the Castle Island Inn – perhaps the most magnificent lawn in all of New England. A “must visit” if you are in Newport.
Similar to its sister island, Martha’s Vineyard, Nantucket is an easy flight or ferry ride away from Boston. The two are vastly different though. I find Nantucket to be a bit more picturesque (the homes are gorgeous!) and a bit more see-and-be-seen style. You can stay close to the main town and you won’t need a car which is nice. Nantucket is the best place to rent some bikes and explore – stop for lobster rolls and sunset drinks at Galley Beach. This island is quintessential New England summer.
Tucked away in the Green Mountains of Vermont, this tiny town is what you think of when you think of fall in New England. It’s the perfect place to spend a weekend away from the city and take in some fresh mountain air. The options for outdoor activities are endless, including everything from mountain biking to hiking to kayaking. Though the town is small, it is home to a few well-known companies such as Ben & Jerrys, Cabot Cheese and Alchemist Brewing. Along with these come fun tours and tastings. There are also a surprising number of great restaurants, given how small the town is.
Set less than an hour from Waterbury, Stowe is one of my favorite winter getaways from Boston. The Stowe Mountain Resort itself is incredibly grand and beautiful, offering everything from a full-service spa (which is amazing, I can attest) to ski school to ice skating to off-trail snowboarding. This mountain is the closest thing we have to a West ski resort. This is a great place to spend a weekend with family or friends and to take advantage of the winter snow here in New England. I find that winter is most tolerable when spent away from the city!
Portland (summer through fall)
Probably one of the more “major” cities here in New England, Portland Maine is such a fun place to visit! Less than a two hour drive from Boston, Portland is a foodie / craft beer / live music / outdoorsy person’s paradise. The number of delicious restaurants and craft breweries are endless – my list of places to try keeps growing. Set on the water, this city really is best visited in summer-early fall. You can go on a schooner, catch lobsters, go hiking, spend time fishing or kayaking…the list goes on and on. I recommend staying in downtown Portland so you can walk to most places. From there, you can hop on boat charters or other local excursions.
Another summer favorite is Portsmouth, New Hampshire. Close enough to be a day trip from Boston but full of enough to spend a weekend here, Portsmouth is a fun harbor town along the coast. You can go on a day trip to Plum Island, walk around the downtown or enjoy any of the many waterfront dining options. Similar to Portland, Portsmouth has great restaurants and quite a few breweries. It’s also right across the border from Kittery, Maine which is the outlet capital up here so if shopping is what you’re into, head this way.
Provincetown (summer, girls weekend)
Better known as “P-Town”, this colorful, lively city is located at the very tip of the Cape. While you can drive there, I prefer to take the fast ferry from Boston Harbor as it’s less than 90 minutes there. Known for their parties and festivals, P-Town is very gay-friendly and such a wonderful, inclusive place to visit. There are endless art galleries, beautiful shops, fun bars with outdoor spaces and great beaches. This town really comes alive in summer and it is one of my favorite locations to take a girls trip from Boston.
Still high on my list to visit are Block Island (Rhode Island), Fire Island (New York), The Hamptons (New York), The Berkshires (Mass), Acadia National Park (Maine) and Quebec City (Canada).