The Best New England Towns to Visit


Article by Helen Phillips

Photography by Helen Phillips

“I haven’t been everywhere, but it’s on my list…” As a born-and-raised Connecticut girl, I’ve spent the past 20-plus years exploring New England. And while I haven’t been everywhere yet, I’ve experienced some truly charming New England towns. Keep reading to find out the best New England towns to visit this fall. If you’re looking to go leaf peeping, apple picking, or just want an adventure, these New England towns need to be on your list! 

Connecticut Towns to Explore This Fall

Easton, CT

Fun fact: I actually lived in Easton, CT, until the age of 7! I lived in this cute little ranch set on acres of property with its own pond and tons of woods to explore! Easton is considered the “Vermont of Connecticut” and for good reason! Easton offers many farms—Silverman’s Farm, Sport Hill Farm, and Sherwood Farm, just to name a few—along with Christmas Tree farms, orchards, idillic scenery, and of course, a quintessential village store. 

Where to Stay

If you’re looking to visit Easton, you’ll want to consider renting an Airbnb or staying in a nearby town, since Easton itself doesn’t have any inns or hotels. My personal recommendation would be The Inn at Gray Barns  (30 minutes away) in New Canaan, CT. If you’re looking for luxurious accommodations, this would be your spot! The restaurant at Gray Barns is amazing (I’ve dined there) and the rooms are incredible. 

Things to Do

Hiking trails abound Easton, CT, and the neighboring towns! Consider checking out Sticks and Stones Grassroots Farm (with well-maintained hiking trails on their 60+ acres open to the public). Go apple picking at Silverman’s Farm, and on your way out, make sure to grab yourself a half dozen of their freshly made apple cider doughnuts! (Sold year-round!)

Essex, CT

This Connecticut River-front town is a charming, relaxing New England destination. It’s a great place to visit in the summer and equally as enjoyable in the fall! Explore Main Street, admire the quintessential New England homes, and walk along the waterfront, all while enjoying the fall foliage! Learn more about all the fun I had on my last trip to Essex, CT, here

Where to Stay

If you’re looking to stay in the heart of downtown, then The Griswold Inn is your place! I had such a nice time getting to know Joan, one of the owners of The Gris, during my last trip to Essex. The Griswold Inn is an incredible family-owned establishment. It provides all the modern luxuries you’d expect, while maintaining its historic heritage. If you’re looking to stay a little out of town, then check out The Copper Beech Inn! I haven’t stayed there yet, but hopefully I’ll have the chance to soon!

Things to Do

When in Essex, you MUST stop by and meet Amy and her husband, Jim, at J.Alden Clothier’s on Main Street. Amy is the sweetest, and her shop has a well-curated assortment of womenswear, menswear, and gifts! Also make sure you check out Essex Park, which is right across the street. It bumps up right to the river, making it the perfect place to picnic. Mosey your way down the street to The Griswold Inn and make sure you check out their wine bar and restaurant, all while brushing up on your history!

Massachusetts Towns to Explore This Fall

Cambridge, MA

On the other side of the Charles River from Boston, you’ll find Cambridge, MA. Home to MIT, Harvard, and more institutions, Cambridge is the perfect blend of city living with a sense of the suburbs. I used to spend a lot of time up in Cambridge, and gosh, what an inspiring place! Harvard’s campus during the fall is a must-explore! Of course, while you’re in the area, you should definitely pop on over to Boston too! 

Where to Stay

As many times as I’ve been to Cambridge/Boston, I haven’t explored too many of the hotels. Check out these 12 best boutique hotels in Boston as of 2019. 

Things to Do

The activities in Boston and Cambridge are endless. While you’re here, though, you have to stop at L.A. Burdicks for the BEST hot chocolate, visit Boston Commons, ride “the T” (subway), explore Harvard’s campus—and those are just a few of the things at the top of my list! Don’t forget to check out Beacon Hill, and make sure you walk down Acorn Street (the most photographed street in Boston, which is even more picturesque in the fall season).

Ipswich, MA

About 45 minutes outside of Boston, you’ll find the cozy coastal town of Ipswich. Surrounded by parks, state forests, and reserves, it’s easy to see why this little spot is considered to be “New England Heaven” by visitors. If you continue out towards the coast, you’ll end up in Rockport, MA, another quintessential New England town that is certainly worth visiting! 

For more information on Rockport, check out my friend Kristy’s blog post, 48 Hours in Rockport, Massachusetts!

Where to Stay

Either stay in Boston or Cambridge and just come up for a day trip, or check into Briar Barn Inn, located just a town over in Rowley, MA. Briar Barn Inn offers rustic comfort blended with the feeling of an elegant retreat. On site you’ll also find their restaurant, Grove, and a spa! 

Things to Do

Ipswich is a must-visit to experience coastal New England in autumn. Russel Orchards Farm is a great destination for apple picking, hot apple cider, cider doughnuts, and more! It’s really a one-stop shop to check everything off your autumn bucket list! While you’re here, make sure you also visit Castle Hill on the Crane Estate. It’s right on the water, and the views are incredible!

Vermont Towns to Explore This Fall

Woodstock, VT

Perhaps the ultimate New England fall foliage destination is Woodstock, VT. This town’s endless charm, ample covered bridges, and amazing restaurants make it an overall 10/10. People actually come from all around the world to go leaf peeping in Vermont! (I learned this on my last trip where I ran into Australians who had planned their trips to coincide with the changing of the leaves.) 

Things to Do

Where do I begin?! You’re going to want to explore downtown Woodstock, check out the cute shops (like the Woodstock Flannel Company), and admire the historic homes. Mon Vert is a great spot for an easy, grab-and-go breakfast or lunch! Worthy Kitchen is a short drive down the road and is my favorite spot for dinner! A little outside of Woodstock you’ll find Queeche, VT. Queechee is home to the Simon Pierce Flagship Store & Restaurant. Make sure you order the hot apple cider, which is delicious!

When in Vermont, you have to visit a maple syrup farm! Sugarbush Farm makes its own authentic maple syrup and cheeses! I’d also recommend taking a scenic drive in Pomfret, VT. Jenne Farm is one of the most photographed spots in New England and for good reason—it’s stunning!

Where to Stay

My personal favorite is The Woodstock Inn. It’s located right in the heart of downtown, it has a fun arcade/game room downstairs, the bar has a great atmosphere, and it’s decorated to the nines during the fall season. If you’re looking for something just as charming, but a little less expensive, then check out the Kedron Valley Inn. I’ve stayed at the Kedron Valley Inn too, and it was very nice!

Manchester + Dorset, VT

Honestly, so much of Vermont is charming and would make for a great trip, especially in the fall. It’s hard to narrow it down! I also am fond of Manchester and Dorset, which are right next door to each other. Dorset is very quaint, while Manchester is a bit more built up and has a lot to offer!

Things to Do

Explore the Equinox Resort when in Manchester. Its grounds are perfectly groomed, and the back patio is a great place to sit on a rocking chair wrapped in a blanket, just enjoying the mountain views (even if you’re not a guest of the hotel). A really fun and exciting activity is doing the Land Rover Driving School in partnership with the Equinox Hotel! I did it a few years ago, and WOW, you really learn how to off-road! Read more about that here

Where to Stay

Of course, The Equinox Resort would be my No. 1 choice, but if you’re looking for something a little more country, then check out Barrows House Inn in Dorset, VT. Barrows House Inn offers guest rooms, suites, and guest cottages on its property. 

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