Travel News New England Road Trip – The Best of the Northeast

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New England Road Trip – The Best of the Northeast

Road trip through history and stunning coastline in New England. Keep reading for our recommended stops.

Find a rental car deal for your New England road trip below.

Maine, Vermont, New Hampshire, Massachusetts, Rhode Island, and Connecticut all make up New England. This trip takes you to 4 of those states, the best cities, shopping, adventures, dining, and places to rest your head. With just about 5 hours of drive time and 292 miles, this road trip will not disappoint. 

Getting to New England

Whether you’re near or far you’ll need transportation cruising through New England. Check out the car rental deals below and if you need to fly in, we have those deals here too. 

Portland, Maine

Portland, MaineFlights to
Portland starting at $73
Car rental in
Portland for
$58* a day
Hotels in

While in Portland, you definitely don’t want to miss the Lucky Catch Cruise or the Victoria Mansion. Those are two vastly different options but I’d suggest the mansion tour in the early afternoon and the cruise after. The cruise takes you on the waters of Casco Bay and you can pull in lobster traps (which you can also have for dinner, yum!) and sight-see lighthouses and historical forts scattered along the Bay.

The Victoria Mansion is a Portland landmark, containing 90% of the original furniture placed in 1860. This guided tour is truly a marvel and something you won’t soon forget. 

Central Provisions

This rustic restaurant serves a variety of small plates and craft cocktails. On the small plates menu, you can find bone marrow toast, Maine oysters, and cod cheek tempura. Their fun and quirky cocktails include signatures like Cardi Bee and Glass Slipper. Don’t take my word for it, this gem has racked up plenty of accolades and achievements that speak for themselves. Stop in, grab a cold one an indulge a little! 

Pomegranate Inn

At the Pomegranate Inn, you can choose from eight guestrooms that each have their own flair and personality. Breakfast is included in your stay and you can expect sample small plates and baked goods like brussel sprouts and bacon hash or Mexican hot chocolate scones. Room rates run from $150 to $400 per night depending on the room and when you stay. 

Manchester, New Hampshire

New Hampshire
Flights to
for $154
Car rental
from $42*
a day
Hotels in Manchester

There are quite a few prestigious museums in the Manchester area, but if you’re looking for something to do other than that, I suggest Massabesic Lake. Permitted activities include fishing, kayaking, and sailing. You can also stay dry and check out the hiking trails. If you’re lucky, you might be able to attend a show at the Palace Theatre, the very venue that used to host the one and only Harry Houdini. 

Castle in the Clouds

Carriage House Restaurant is located inside the Castle in the Clouds. You can enjoy lunch or dinner outside on the terrace under an umbrella with views of the breathtaking mountain landscape. On the lunch menu, you can expect to find sandwiches, tacos, soups, and salads. While this restaurant serves up good food, the atmosphere is what you’ll remember most.

Ash Street Inn

This historical looking house has a modern take on the inside but still maintains unique features like the colored glass windows. Guests can choose from five newly remodeled rooms and can expect breakfast in the morning. Breakfast is served in the dining room, but unlike most B&B’s, Ash Street cooks everything made to order from their provided menu. After breakfast head out and enjoy the best Manchester has to offer.

Boston, Massachusetts 

Flights to Boston
for $74
Car Rental in
Boston from 41*
a day
Hotels in Boston

Fenway Park, Harvard, and Chinatown are a few of the more well-known hot spots in Boston and ones that you should put on the agenda. If you’re visiting during baseball season then catch a game at the iconic Fenway Park. Even if you don’t have plans of attending Harvard in the future, there are still tours available for you to check out the prestigious university. Chinatown holds some of the best Chinese food in Boston so stroll through the neighborhood and try to hit as many of them as you can. 


Oleana is a Mediterranean style restaurant with amazing bites. They have quite the wine list and the dishes are picture-perfect – seriously, bring the camera. On the menu, you can find traditional choices like octopus, hummus, and pitas and more unique entrees like Spoon Lamb en Croute and Vermont Quail Kebob. Don’t leave without getting dessert! They have Peach Lambic, Turkish-Style Profiteroles, and more. 

Liberty Hotel

The Liberty is a luxury hotel in the heart of Boston that you can’t miss with its extraordinary exterior. Just steps from shopping and other attractions, the Liberty is not your average hotel. The Liberty Hotel has a unique history and was once a jail! -(Charles Street Jail).

Cape Cod, Massachusetts

Cape Cod,
Flights to Boston
from $74
Car rental in NantucketHotels in
Cape Cod

Cape Cod is all about the outdoors and the lighthouses. There are dunes, boat tours, trails, and beaches just waiting to be explored. Wellfleet Bay is one of the best sandy spots along the coast of Cape Cod to either relax onshore or hike the trails in the dense forests at the shore. Another cool spot to check out is the Cape Playhouse, where stars like Betty White, Jane Fonda, and Bette Davis all got their start. 

Cape Cod, Massachusetts
Cape Cod, Massachusetts

Pie in the Sky

This little bakery is well-known for their breads and pastries. They offer breakfast and lunch too, but their pies really get the crowds coming. They have apple, blueberry, chocolate mousse, key lime pie, and a daily special. Also baked fresh daily are popovers, cookies, brownies, and scones. 

Belfry Inn

Guests can choose between three unique buildings when considering the Belfrey. There is The Painted Lady, The Abbey, and The Village House. The Painted Lady is a large Victorian-style home with a pink exterior and 10 rooms to choose from. The rooms have a more modern appeal. Breakfast is included and is served in the Bistro located in the Abbey building just a few steps next door. Speaking of The Abbey, this building gives off a church vibe and has six different rooms to choose from and have a more preserved look. Lastly, The Village House is equipped with 4 bedrooms, each sporting their own personality. 

Newport, Rhode Island

Newport, Rhode IslandFlights to Newport
starting at $39
Car rental from
54* a day
Hotels in

There are so many opportunities to enjoy live music in Newport that it’s tough to narrow down the best spots. There are loads of bars and dancing for those who enjoy the nightlife. If you want to keep the party going, there is the Tiverton Casino in town. For some family-friendly experiences, you can choose from horseback riding, harbor tours, and helicopter rides. 


This fine-dining French-inspired establishment is perfect for that five-course meal you’ve been waiting to treat yourself to. Start off with one of the chef’s recommendations, Tartare du Saumon, and move onto Escargot for your starter. Next, the Salade aux Poires before the main course – Homard et St. Jacques Cardinal. Finish off with a dessert Mousse à la Vanillé and you will truly be satisfied. Don’t worry, all descriptions are provided on their menu. 

Ocean Romance Bed & Breakfast Yacht

All aboard this one of kind B&B yacht with 3 bedrooms which is located in the Goat Island Marina and in walking distance to attractions in Newport. This yacht does not charter, but rather stays docked for guests to rest their head and then wake up to a home-cooked breakfast. 

Newport, Rhode Island coast
Newport, Rhode Island coast

Maine to Rhode Island

Well, now that you know how to get there, what to do, where to eat, where to rest your head, what are you waiting for? Most activities mentioned in this article are geared for summer but there are plenty of winter wonderland activities to plan for as well!