Travel blog, USA

New England road trip itinerary

New England road trip Itinerary Maine Cape Elizabeth-min

Road trip in the USA are not only popular in California or Florida. A New England road trip is also a good idea to discover the beautiful, wild and green region.

Below you will find our New England Road Trip itinerary to eat your way through the region!

Where is New England?

New England includes six states of the United States: Maine, Vermont, New Hampshire, Massachusetts, Rhode Island, and Connecticut. It overlooks the Atlantic Ocean, bordering Canada to its North and the State of New York to it’s South West.

Apart from being popular for its nature, it has been a surprise to discover there is a lot of excellent food too: sea food mostly, but not only!

Since is not a huge area, renting a car is probably the best option to experience those places. It gives you all the freedom to explore, be flexible and open to some changes of plan! A always for a roar trip I recommend you to book Sunny Cars for all inclusive insurance and best prices.

Driving through New England is like a fairy tale, you will drive through forests, little villages, lakes and mountains. 

Weather is very variable, we have been in June and we found some rainy and windy days. Be prepared for colder weather even in summer!

New England road trip Itinerary : Boston

Boston is a very quiet city with open wild spaces and a lot of green parks. Architecture changes a lot from neighborhoods to neighborhoods. There is lot of history, museums and two of the best university of the country, Harvard and M.I.T. Since is not a big city, each neighborhoods are easily walkable. Read our article on what to do in one day in Boston for more informations including the Skyline observatory, a tour of Back Bay and a food tour!

Where we stayed: we stayed at the Revolution Hotel. An hostel type of hotel with shared bathroom. It is a good option because of the price and its very central location!

Maine : Portland and lighthouses

The second stop of our New England itinerary was Maine, the largest of all New England’s States.


At sunset time, we arrived in the little and peaceful town of Ogunquit, popular for its almost 5km of sandy beach and stylish wooden houses in pastel colors with enticing flower gardens. Not a coincidence Ogunquit name means “beautiful place by the sea”!

As it is mainly an holiday destination, the area offers lot of outdoor activities like golf, sail, kayak, surf, or paddleboard and boat tours along the bay.

Restaurant pick: “Jonathan’s Restaurant”, a name with 41 years of history and experience. Atmosphere and food are a real highlight here. Products are local or even coming form their own farm in South Berwick. On the menu: great cocktails, oysters, lobsters (rigorously from Maine) and the award winning chocolate mousse!

New England road trip Itinerary Maine Ogunquit 1-min
New England road trip Itinerary Maine Ogunquit-min


Left Ogunquit we drove to Portland, the beautiful harbor city. 

Although it is the biggest city in Maine, it only hosts about 66K inhabitants, most of them very friendly and keen to start a funny random chat with you.

The most picturesque part of Portland is the downtown district: narrow cobblestones streets; red bricks buildings; curious shops of souvenirs, clothes and porcelain; restaurants on the mole and apparently a great nightlife as its full of pubs!

Portland food tour

In Portland we had our second Food Tour, organized by the two very enthusiastic guys of “Maine Foodie Tour”. They look quite proud of the quality and history of the food in Maine – and more specific in Portland, and are very happy to show us around. Few curious things we learned during the tour: Donuts in Maine are very popular and… different! The moistness come from smashed potatoes, best shop to try is The Holy Donut, were people are ready to queue for more than 30 mins just to buy ones there! Lobster in Maine is of course a flagship and becomes one of the symbol of the State. They are different from other lobsters as they have one claw smaller than the other.

Here the stops included in the Food Tour:

Maine’s Pantry, this family business shop is a grocery store with a bakery corner (where potato donut are also served) and great coffee. Ideal if you want to buy some high quality local food to bring home with you!

Thirsty Pig, for sausages lovers! They actually also have a vegetarian sausage option but the main menu is composed by handmade meat sausages. Very interesting is the combination with their sauces. They even serve sausage with blueberry sauce! A note goes also to the great selection of beer, only from Maine.

Public Market House, former farmer-market area, is now home to a variety of restaurants from all over the world on two floors. For something exotic try the Mr. Tuna Sushi Roll at Tamaki Sushi; special ingredient is the Jonah Crab, a special crab from Maine.

Gritty McDuffs, sip one of their craft beer while eating the mandatory lobster roll!

Stonewell Kitchen, grocery store since 1991. They sell their own products only. Blueberry jam is like heaven – less sugar and more blueberries is the secret,  and it is still their most sold products!

Dean’s Sweets, for some fine chocolate in interesting combination. Most curious is chocolate filled with coconut and potato.

Length of the tour is 3 hours. Price of the ticket is about $79 pP. For more info visit: Maine Foodie Tours

Cape Elizabeth

After the food tour, we had the plan to cruise around a few Lighthouses in Portland. We didn’t have much luck though and due to bad weather our cruise got canceled. We decided to wake up earlier the next day and to drive till Cape Elizabeth to see the Portland Head Light, one of the biggest and oldest Lighthouse in Maine (it operated since 1791). Driving till the Lighthouse actually turned out to be a good option, as we had the time to walk around the park and get very close to the Lighthouse, thing that wouldn’t be possible during on a cruise. Definitely and worthy landscape, 20 mins only far from Portland. 

Restaurant pick: Boone’s Fish House & Oyster Room have a try of their Oyster and Mac’n’Cheese Lobster or Lobster Roll : the Lobster sandwich with sweet bread!

Where we staid: Hyatt Place Portland-Old Port Specious room and bathroom. What I loved about this hotel is the huge window right next to the bed that oversees the city. If you are on higher floors, you can see the sunrise from the ocean just from your window! Amazing way to wake up early and make a good use of the jet lag ;)!


We left the ocean view of Maine to head to the fresh and green mountains of the New Hampshire. 

We drove through the White Mountain National Forest, which covers one quarter of the entire State. I can only imagine how wonderful the landscape must be in autumn when the foliage starts and the colors change in red and yellow, in between lakes and waterfalls.

The highest mountain of the White Mountains is Mt. Washington, with its 1917m of altitude, located in in the Crowford Notch State Park.

The summit is reachable by car (in summer only), via one of the few hiking trails (it may takes 4 to 5 hours) or, option that I preferred, with the world first mountain-climbing cog train! 

In almost one hour at a speedway of 4.5km/h, the cog train covers a difference in altitude of almost 1,100m. Hold on well! The pendency is so intense that will be very hard to stand up! 

Needless to say, the view during the ride is breathtaking. Once arrived on the peak, you have a 360° spectacular view over mountains and the valley. They said on clear day you can even see the Atlantic Ocean, that is almost 112km away!

On the top there is a bar, restaurant and a souvenir shop. There is also a weather observatory station, that makes this incredible scenario even more suggestive.

Bring warm clothes as it can be very cold and windy once on the top.

For info about the cog train ride visit: theCog

New England road trip Itinerary white mountains 2-min

Lunch suggestion: for a quick lunch try “The Local Grocer” in North Conway. You can have fresh and healthy smoothie, local and organic food and products in the green landscape of the mountain. Possible to sit both outdoor or indoor.

Where we staid: The Glen House Hotel, although the name Glen House has been around for almost 130 years, this specific hotel is absolutely brand new (it opened last September). For mountains lover, is a dream waking up which such a stunning view over the mountains. The cure for details in the interior design and the service is remarkable. 

This hotel is special also for the effort in being the first sustainable hotel in the New Hampshire. Almost self-sufficient, they use geothermal and hydro energy for their heating and electricity needs; low energy consume LED lighting; minimum usage of plastic in the rooms thanks to refillable shampoo and shower gel bottles. They even invite you not to waste your soap, providing a package to bring it with you. 


On the 5th day of our road trip, finally we arrived in Vermont!

For the open and wild landscapes, the kindness of the people, the strong culture and passion for food, Vermont is probably my favorite State of New England.

Vermont has got many local food producers and grocery shops and restaurants make a big effort to promote and support them by offering mostly local products.

The most famous product is maple syrup, of which Vermont is nation’s leading producer. Alone it generates 47% of the country’s maple syrup (nearly 7.5M liter)!

On the way to Burlington we made our first stop to Morse Farm Maple, a family business that since 7 generations is specialized in the production of Maple Syrup and any sort of products based on that. 

A little note on Maple Syrup : it is healthier and sweeter than sugar, it is an antioxidant and contains magnesium, potassium and vitamins. You can find it if a variety of products like butter, mustards, seasoning for salad, jam, cookies, candies and much more.


With its 42K habitants, it is the largest town in Vermont – bigger than the capital of Vermont, Montpelier. 

Here is nice walking on the outdoor pedestrian shopping and dining mall. On Saturdays, there is the Burlington Farmers Market on the Burlington’s City Hall Park.

You can continue your walk till the Lake Champlain. This lake is a natural border for the three States of Vermont, New York and Quebec. 

Restaurant tip : The Foam Brewer

After a long walk, there is nothing better than drinking a fresh beer! The Foam Brewer is a beautiful spot with the lake view. Very interesting and unusual their rotating menu, which is changed about twice in a week! Looks like they really like play with flavor, mostly they add fruits flavor like blackberries and lime or grapefruit and dragon fruit and even salt seawater as ingredient!

Another tip for Burlington is : old Soda Plant. It is a huge area home to 30 small businesses, galleries, art studios, shops and restaurants. It is still under construction and many shops will open in the near future. If you plan to come here, make sure to have a coffee at Brio Coffeworks . Their coffee is really tasty and it is interesting to see the toasting process.

Look at the The Soda Plant for more info about this project!

Restaurant pick: The Great Northen is really a gem! Great food prepared with local ingredient, it turned out to be a really yummy surprise!

New England road trip Itinerary Burlington 1-min


If you like ice cream and you are in Vermont, you can’t pay a visit to Ben & Jerry factory.

Situated in Waitsfield, is not the biggest factory they have, but is the only one open to public and that organize group tour.

The tour is about half an hour and after an introducing video of Ben & Jerry history, you visit the production site where how about 300k cups of ice cream are produced in a day!!

Head to the “flavoroom” to check all the latest new flavors and to have a scoop of the “not-released-yet” new taste!!

New England road trip Itinerary Ben & Jerry's 2-min

Last stop of our New England’s road trip itinerary : Woodstock

The last town we visited is the cute and picturesque town of Woodstock, situated in the heart of the Green Mountains. It so small that you can easily see the whole town by bike. The wooden houses are so pretty, you will have the feeling to be in an old movie. 

New England's road trip itinerary Woodstock 1-min

Some stops we did on the way:

  • Bundy Modern art gallery a modern art gallery presenting work of contemporary artists and sculptures. Open to the public on the weekends only.
  • Mad River TastePlace a grocery store ambassador of local artisan food and drink. The owner, Robin Morris, likes to talk a lot about how many small and good producers is supporting and their stories. Part of the project is also helping artisans starting their own food businesses through the Mad River Food Hub;
  • Caledonia Spirits, local producer of Gin and Vodka; 
  • Long Trail Brewery & Co, for beer lovers;
  • Billings Farm Museum, is an open farmhouse, goats and sheep and 120 cows. You can plan a tour and taste some cheese. In the farm museum, you visit the old home of the farm manager with interesting story about how people were living in the 1890.

Restaurant pick: Worthy Kitchen, delicious variety of hamburgers and cocktails with a nice view on the Green Mountains.

Where we staid: The Woodstock Inn & Resort, this resort is an huge complex hosting two restaurants, bar, gym and sauna. The room are very spacious and in perfect style with the vibe of the town. Use the bike they offer to their guests to go around Woodstock!

Woodstock was the end of our New England road trip itinerary!

It has been truly wonderful to discover all these places, we thank Brand USA and LMG Management for the invitation and fun time!*

*Written by Stefania Casiraghi

**All opinions remains our own