New England Summer Seaside Towns You Don’t Want to Miss
While New England “offers” us a variety of weather all year round, every summer we’re reminded that we don’t always have to travel far to have an epic trip. Summer is the perfect time for a roadtrip or long weekend through some of our favorite coastal towns. And since Boston is only an hour or two away from most of these stops, you’ll be eating lobster rolls and relaxing on the beach in no time.
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Our Favorite New England Destinations
All of these spots are great for their own long weekend, but if you have the time, a roadtrip through several is definitely the way to go. Boston Logan International Airport has flights from all over the country and world and once you pick up your rental car, you’re only 90 minutes from our first stop!
Our Favorite New England Beach Town Destination – Ogunquit, Maine
Take 95 all the way to Wells and then hop on Route 1 and you’ll find yourself in the small but hopping town of Ogunquit about 45 minutes south of Portland. Ogunquit offers some of everything: shopping, beaching, boating, live music, theater, restaurants, and even a drag show (Bonus: Ogunquit is queer friendly)!
What To Do:
1. Ogunquit Beach
The beach in Ogunquit is wide, long, soft and offers a great place for relaxation or for playing. Rent a surf board at Liquid Dreams or relax in an Adirondack chair and watch the waves come in.
2. Arts and Theater
This small town isn’t just for the beach, it offers an American Art Museum (right on the water, too – so you’re not missing out on those views!) and a seasonal theater bringing Broadway-level shows to Maine for over 90 years! The Ogunquit Playhouse runs multiple shows a summer, each running for about a month. This summer’s line up includes Guys and Dolls, High Society, and When Elvis Met the Beatles (not to mention three children’s theater shows). We saw the show Cher here a couple of summers ago and it was outstanding!
3. Eat and Drink
There’s no shortage of bars and restaurants to check out while you’re in town. They have everything you can think of from a Brazilian steakhouse, to Mexican, Italian, and of course New England, fresh seafood. Some of our favorite places include: The Rose Cove Cafe for a romantic dinner, That Place, for drinks and apps, Barnacle Billy’s for excellent Rum Punch and fried seafood, and The Scoop Deck for ice cream – try the Milky Way! And of course, you must stop into The Front Porch, a dueling piano bar with live music, entertainment, and great food and drinks. It feels like there’s always a party upstairs!
4. Perkins Cove
There are plenty of shops to stop into as you walk the streets in Ogunquit, but set apart (in a cove, no less), is Perkins Cove on the south end of Rt. 1. Perkins Cove has its own (paid) parking, many shops and restaurants to stop into and is right on the water/marina. Perkins Cove brings you that quaint New England seaside town feel in a small area. It’s also the starting point for the Marginal Way, a 1.25 mile paved cliff walk that overlooks the Atlantic with benches along the way and is the back drop for several hotels. A must-do if you’re stopping in Ogunquit.
Where to Stay:
Anchorage by the Sea – waterfront resort with Marginal Way access
Meadowmere Resort – eco-friendly with pools, close to downtown
The Trellis House – stylish B&B steps from Ogunquit Beach
Our Favorite New England “City” Town Destination – Portsmouth, New Hampshire
You can take Rt. 1 south (or the more scenic Rt. 1A) to the much larger, Portsmouth, NH. Portsmouth makes our list as favorite “city-town” because its year-long population and general size are much bigger than the other spots on our list, but don’t be put off… Portsmouth is still a quaint and historical seaside destination. Between the shopping, bars and restaurants (Portsmouth has one of the highest ratios of restaurants per capita in the country!), music and arts summer-long festival, and quaint feel, you might not want to leave!
What To Do
1. Stroll
The brick sidewalks, the winding alleyways, the historic charm – this city is made for walking. Stay in any one of the downtown hotels, inns, or bed and breakfasts, and you can walk in either direction to find unique shops, local restaurants, “the decks” (over water bars and restaurants), Prescott Park with live music and a seasonal show, and of course coffee. There are easily close 10 ten coffee shops downtown (though our favorites are Kaffee Vonsolln and Cafe Kilim).
2. Eat and Drink
As I mentioned, there’s no shortage of places to eat or drink in Portsmouth and you would be doing your self a disservice to miss out on the the dining scene here. With every type of food you can think of and ambiance for days, there are few bad choices here. We loved: Cafe Mediterraneo, The Goat (with live music most nights, great burgers, and epic “sledgehammer” mimosas for breakfast), The Friendly Toast for breakfast, and don’t miss a famous Jimmy Juice at the Old Ferry Landing deck on Bow St (also check out the fried seafood here!). Also check out the rooftop bar at Envio for panoramic waterfront views.
3. Music, Arts, Festivals, and More
Prescott Park has everything you need in the way of entertainment in the summer. All summer long, the park offers free shows and entertainment (a suggested donation is encouraged), from Grammy-winning artists every Wednesday night, a seasonal play (this year is Freaky Friday), and movie nights! Prescott Park also hosts a number of festivals throughout the summer including the annual Chowder Festival where you can sample many local seafood chowders.
Jimmy’s Jazz and Blues Club on Congress Street also offers nightly entertainment with even more award-winning performers. Jimmy’s is an upscale Jazz bar where you can book a table for dinner and the show. This one isn’t free but it offers reasonably priced shows and is always a good time.
There seems to always be live music somewhere downtown, here. From buskers to restaurant live music, just walking around you’ll find some. Check out The Press Room, The Music Hall (bringing music, comedians, movies and more from some of the biggest stars like Shania Twain this summer), Strawberry Banke’s Tuesdays on the Terrace series, and Summer in the Streets on Pleasant Street on Saturdays.
4. History
Portsmouth is old… 1623 old! And it’s found interesting ways to showcase its history. For starters, Strawberry Banke Museum is an interactive neighborhood, celebrating 350 years of history. Each house you enter tells its own story, with re-enactors, and artifacts. A must-do! Discover Portsmouth as part of the Portsmouth Historical Society, is located downtown and offers tours of many historical homes as well as daily bike, walking, and Segway tours of the area.
Bonus:
If you have extra time (or a rainy day), head 15 minutes up Rt. 1 to the Kittery Shopping Outlets!
Where to Stay
The Hotel Portsmouth – charming inn in a Victorian mansion
Residence Inn Portsmouth Downtown – modern, walkable location
The Bow Hotel – boutique hotel inside an old brewery
Our Favorite Gilded New England Town Destination – Newport, Rhode Island
The last stop on our New England destinations list is Newport, RI and it does NOT disappoint. Newport is by far one of our favorite spots in New England and offers a little bit of everything. We’ve been a couple of times and each time we find something new to do, see, or eat!
What To Do
1. The Mansions
As obsessed as you are with the HBO show, the Gilded Era Newport mansions will captivate you, too! You might even recognize some of the filming locations. Each more ornate than the next, owned by various members of the Vanderbilt family and friends, Newport served as a summer “cottage” hotspot for the wealthy of the Gilded Age. Take a tour through as many as you can to be transported back in time. Bonus tip: Take time to walk the Newport Cliff Walk and see the backyards of many of these mansions for free!
2. Explore
Maybe its a trolley tour up Ocean Drive, walking around the marina/port area, or strolling up and down the historical streets, there is plenty to explore in Newport. The historic Ocean Drive and Bellevue Avenue takes you by the famous Gilded Age mansions but also the “houses” (they’re still mansions!) of today’s residents. Also walk through the Salve Regina University’s pristine campus.
Next, head downtown and make your way up and down the streets exploring local unique shops and swing into the International Tennis Hall of Fame with museum and active court for members.
Finish up down by the marina for some waterfront dining and even more local shops. Scope out the yachts and Clarke Cooke’s House for dinner and drinks near Bannister Wharf.
3. Eat
We’ve never had a bad meal in Newport and there are so many restaurants to choose from. Our personal favorites: Cru Cafe (seriously… don’t eat breakfast anywhere else!), The White Horse Tavern (America’s oldest Tavern), Diego’s Newport, and the Fastnet Pub for drinks and entertainment after dinner!
There are plenty more spots to hit serving a range or cuisines including New England seafood (are you sensing a theme with this tour??).
4. Castle Hill
While it wasn’t exactly in our budget to stay at Castle Hill, but this gorgeous hotel and restaurant set by the seaside is a must do. Sip wine and cocktails on their expansive lawn (Adirondack chairs are available if you’re lucky or reserve them), watch the boats come into port, and feel like you’re living the high-life for a bit. It’s worth the drive.
Bonus tip: Want to save for splurges like this? These budget travel hacks helped us stretch every dollar.
Where to Stay
The Attwater – stylish boutique hotel near the Cliff Walk
Hotel Viking – luxe with rooftop bar and spa
The Wayfinder – trendy, art-forward with coastal touches (and our personal budget favorite)
Our Favorite New England Historical Town Destination – Mystic, Connecticut
As we head south on 95 on our New England summer road trip, your next stop should be in the town of Mystic, CT. You may remember, Mystic from the Julia Roberts movie, Mystic Pizza (and yes, it really exists!), there’s so much more to check out!
What To Do
1. History
Mystic is chocked-full of maritime history and you can experience some of it on a tour of the recreated Mystic Seaport Village. There are re-enactors, historical buildings to visit, demonstrations by coopers, printers, and silversmiths, not to mention history about the over 600 ships that were built here over the years.
The downtown district is also historical with historical, colonial homes of former sea captains, historical gardens, sculptures, and landmarks. Also check out the many American history museums, Native American history museum, and Submarine Force Museum, home of the USS Nautilus.
2. Shop
The Olde Mistik Village is your spot for local shops. This open “air village” is a little corny in its historical attempts, but the shops here are unique, there’s good food and drink, and I always leave with something I didn’t know I needed!
3. Unexpected Scores
The weekend we spent in Mystic was rainy and cold, which limited a lot of our outdoor experience (we were wimps!), but it also led us to some unexpected finds. For instance, Mystic has an aquarium with thousands of different species. There are also many different wineries and breweries in the area. We enjoyed Stonington Vineyards and Maugle Sierra Vineyard. There were also outstanding restaurants and bars like Via Emilia and Taquerio Mexican Restaurant.
Where to Stay
The Whaler’s Inn – historic charm in downtown Mystic
Hyatt Place Mystic – family-friendly and convenient
Captain’s Mansion – luxury stay with coastal vibes
New England Is Your Summer Bucket List
From windswept beaches to lobster rolls and Gilded Age glamour, coastal New England is packed with personality. Whether you hit all four towns or pick one for a long weekend, this road trip is unforgettable — and delicious!
Got questions or a favorite town I missed? Drop it in the comments or DM me on Instagram @TheWandercents.
Planning your trip now? Pin this guide so you don’t lose it when it’s time to pack your bags.
