Thinking about taking a New England road trip this year? If so, I’ve got you covered!
In this post, I’m rounding up 9 amazing destinations in New England that are worth visiting on your next road trip. These destinations aren’t necessarily the most visited places like Boston or Newport. Some are more off the beaten path, but the discoveries that await you will make the journey worth it. And the best part? If you live in the region, you can easily visit these destinations over a long weekend.
So grab your map, snacks, and buckle up for some great New England road trips this spring and summer.
9 Destinations for Your Next New England Road Trip
1. Kent, Connecticut
If you’re looking for a weekend full of nature and tranquility, head to Kent, Connecticut. Located on the western edge of the state, just across the border from New York, Kent is one of Connecticut’s hidden gems. The rural and small-town feel is a welcome change if you’re looking to escape the hustle and bustle of NYC or other urban areas nearby.
There are so many things to do in and around Kent. Head outside for some great for hiking, biking, or fishing. If hanging in town is more your speed, lose yourself in a book at the House of Books shop, go antique shopping, or enjoy all of the culinary options the region has to offer. Treat yourself to a pick-me-up at Kent Coffee & Chocolate, or sip some brews at Kent Falls Brewing. And make sure to check out Swyft for wood-fired pizzas and seasonal fare. (Right now during the COVID-19 pandemic they are doing take-out only but check the website for updates.)
Related: Why it’s worth taking a road trip to New Haven, CT for the pizza.
2. Providence, Rhode Island
I think Providence is one of the most underrated cities in New England. And it’s such a great destination for a New England road trip, especially if you love food! There are so many great culinary options in this city. In fact, my husband and I spent 48 hours basically eating our way through the city, and I wrote an entire blog post about it!
Related: Check out my Foodie’s Guide for Providence, RI
Beyond the food scene, Providence is full of history and culture. And the city is small enough that you can easily explore much of it on foot. Or by boat! Two great options for learning more about Providence include Providence Walks, self-guided historic walking tours created by the visitors’ bureau, and the open-air cruises offered by the Providence Riverboat Company. (They have also teamed up with Rhode Island-based Gooseneck Vineyards for a Twilight wine-tasting cruise that I can’t wait to try!)
Last but not least, visit the Providence Athenaeum, a 200-year-old library that is home to incredible collections and rare editions from famed authors such as Louisa May Alcott and Walt Whitman. And an interesting historical fact – it’s also where Edgar Allen Poe was dumped by his fiancée!
3. Mid-coast Maine
If you love exploring a rugged coastline dotted with picturesque lighthouses, and eating lobster fresh off the boat at casual lobster pounds where it’s almost always BYOB, then you need to plan a road trip to Maine this summer. There is so much to do and see (and eat!) in mid-coast Maine, that I consider it one of the best New England road trips that you can take.
I finally made it to mid-coast Maine last summer on a week-long road trip and now I can’t wait to go back. We squeezed in so much during our time there, including kayaking, fishing, exploring old forts, swimming at local beaches (Popham Beach is my favorite), and eating lobster, so much lobster!
If you’re curious to know more about planning a road trip to Maine, I wrote an entire post about the best places to visit in mid-coast Maine.
4. North Adams, Massachusetts
I feel like North Adams is the town in the Berkshires that nobody really talks about but is definitely worth visiting if you’re planning a New England road trip. North Adams is located in the northwest corner of the state, very close to the Vermont and New York state borders.
Known as the smallest city in Massachusetts, North Adams is a vibrant community full of art, culture, and history. While there are so many great things to do in the area, one of the highlights for sure is the Massachusetts Museum of Contemporary Art, known as MASS MoCA. It’s one of the largest centers in the United States for evocative and contemporary visual and performing arts.
The museum was built in an old printing works factory and now is home to incredible film, theater, music, and dance as well as contemporary art. The museum has changed its visiting guidelines due to the pandemic. Make sure to check the website before you plan your visit.
5. Outer Cape Cod, Massachusetts
Outer Cape Cod, or the northernmost section of the Cape, is one of my favorite places on the planet. Of course, I might be a little biased since I’ve been visiting the region for more than 20 years, always staying with very close friends who have a house there. But putting my personal connections to the area aside, Cape Cod is a place that everyone should visit at least once.
What is so great about Cape cod? For one thing, there’s the natural, rugged beauty of this sandy peninsula surrounded by the sea. This is part of what has drawn so many artists to the area, particularly the colorful community of Provincetown, at the very tip of the Cape. Then there’s the laidback nature of the Cape. I live in NYC, where most people escape to the ritzy and scene-filled Hamptons in the summertime. The Cape is the exact opposite of the Hamptons and that’s why I love it. What the area lacks in pretension it makes up for with incredible food, (Wellfleet Oysters are my favorite!), art, culture, and beautiful beaches.
If you want to plan a New England road trip to the Cape, I highly recommend staying either in Wellfleet, Truro, or Provincetown to fully experience what life is like on the outer cape.
Make sure to check out my Outer Cape Cod travel guide for all of my tips and recommendations, including where to stay and eat!
6. Woodstock and Quechee, Vermont
Most people who live in the northeast head to Vermont in the wintertime to go skiing. But guess what? Vermont is the perfect place to plan your New England road trip year-round because the scenery is magnificent no matter the season, and there’s always something to do!
Two neighboring towns in particular that I love are Quechee and Woodstock, Vermont. I first visited these quaint and quintessentially Vermont towns when I was a student at Dartmouth College. The towns are only about a 20-minute drive from campus, so my girlfriends and I would often jump in the car on a Saturday afternoon to go visit. We always had so much fun checking out the covered bridges, the stately Vermont homes, and the white stapled churches.
Woodstock, in particular, is known for its cute shops and restaurants, with a charming downtown. Quechee is known for the famous Quechee Gorge, a large antique mall, and its many cheese shops. (Can you ever go wrong with cheese?!)
But perhaps one of the best-hidden gems to visit in Quechee, (and my favorite place to go when I was in college) is Simon Pearce, a glassware shop, glass-blowing studio, restaurant, and bar. It is so cool to watch the artisans at work, creating beautiful glassware. And the restaurant is where we always went to celebrate special occasions. The food is outstanding and, yes, you get to enjoy all of the glass and dishware made on the premises during your meal.
7. Portsmouth, New Hampshire
About an hour northeast from Boston, (an easy road trip for Bostonians!) is one of New England’s most popular harbor towns, Portsmouth, NH. Whether you want to eat and shop your way through town or learn more about Portsmouth’s culture and history, there’s something for everyone.
Culinary standouts include La Maison Navarre for French pastries and crepes at breakfast, or the French wine and bistro food at night, pizza at Flatbread Company, coffee and drinks at Book and Bar, and finally, Cure for American comfort food.
For a bit of history, check out the Strawberry Banke Museum which details the origins of the Portsmouth settlement and how the original colonists fared during settlement times.
Last but not least, explore the many cool shops in Portsmouth. Don’t feel guilty if you buy anything because everything is tax-free since New Hampshire has no sales tax!
8. Westerly, Rhode Island
Westerly, RI is close to Newport, RI but there’s a world of difference between these two seaside towns. While Newport is classy and upscale, Westerly is laid back and fun. I had the best time when I visited Westerly because there are so many fun things to do there.
First, there’s the beach. (If you read this blog, then you know how much I love the beach!) Then there are tons of casual beach bars and eateries you can hit up straight from the beach, sandy and still in flip-flops. (We went to Windjammer Surf Bar which has a patio that overlooks the ocean.)
Related: Everything You Need for a Day at the Beach
And maybe the best part, (and what made me super nostalgic for my childhood) are the two adventure parks. You can live out your childhood fantasies playing miniature golf, riding bumper cars, shooting down water slides, and more. I also highly recommend driving along the coastal road to see some beautiful homes as well as the stunning Weekapaug Inn.
9. Portland, Maine
Have you have never been to Portland? If not, then put this city at the top of your list for New England road trips. Portland is such a fun city with a burgeoning food scene that keeps getting better and better. There are also ample outdoor activities you can take advantage of in the city. Go for a bike ride or take a gander along the Eastern promenade. And make sure to check out the city’s famous lighthouses. Two of the most popular ones to see are the Portland Headlight, and the Portland Breakwater Lighthouse (Bug Light).
But back to the food. If you make it to Portland, these are the places you must visit for the food. Head to Standard Baking Co. in the morning for freshly baked pastries and bread. Get oyster and lobster at Eventide Oyster & Company. Wait online (yes, there’s always a line) for an afternoon pick-me-up at one of The Holy Donut’s two locations for potato donuts. And for dinner, check out Central Provisions for outstanding, small shared plates or well-known Fore Street, the restaurant that arguably kicked off the food scene in Portland when it opened 20 years ago.
Are You Ready to Plan a New England Road Trip?
I hope that this round-up of 9 awesome destinations in New England has inspired you to take a road trip. I have to say, after writing this, I’m now excited to plan trips back to all of these places.
Let me know if you have any questions and have fun planning your New England road trips!
Looking for more fun road trip ideas? Check out these travel guides for Upstate New York:
A weekend roadtrip to the Catskills
Everywhere to eat in Woodstock, NY, and Everything to see & do in Woodstock, NY
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