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New England Road Trip

by John the Wanderer
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a beach with rocks and water

New England Road Trip

This article is New England Road Trip. It is the introduction to my wife and my road trip exploring six states in New England over a five day period.

New England Road Trip

Our New England Road Trip will be a multi-part trip report highlighting our experience getting to and from the Northeast, as well as while we were exploring the area.

New England Road Trip

It will cover our flights, hotels and some of our dinning experiences.


Being John the Wanderer, you know that I like to go out and explore places.

Typically that means checking out large cities and beach destinations.

This was the first time I got to experience a different part of the country.

New England Road Trip

The trip started when my wife had a meeting scheduled in Providence.

American Airlines Washington Providence New England Road TripAmerican Airlines Washington Providence New England Road Trip

We looked and discovered how inexpensive airfare was to that airport ($250 on American Airlines), so we thought it would be perfect to add on days, rent a car and explore the area.

New England Road Trip

Looking at a map, we thought it would be great to spend time in the Berkshires, Cape Cod, Portsmouth and Newport, because of the awesome images we saw online.

New England Road Trip

Book your next trip: Agoda, Apple Vacations, Booking.com, Edreams, Expedia, Hard Rock Hotels, Hilton, LivingSocial, Loews Hotels, Momondo, Priceline, Radisson Blu, or TripAdvisor.


The Berkshires was our first stop on the road trip.

We went on TripAdvisor and saw all the beautiful images others uploaded about the communities, hotels and restaurants and knew it was an amazing first stop on our New England Road Trip.

With it’s charming hotels and inns and great restaurants, you can’t go wrong visiting.

We also visited Lonely Planet and fell in love with the place.

From the first image on the page showing the field of lush green trees, mountains and more, we couldn’t help but get excited for a visit.

Did you know that the Boston Pops perform at a retreat in the Berkshires each summer?

Also the area is filled with great art, from museums to music to culture and history the Berkshires are an amazing place to visit.

Make sure you check out 1Berkshire as well when making your plans.

Chambery Inn New England Road Trip

We decided to stay at the charming Chambery Inn where we got to stay in a schoolhouse and have a great picnic breakfast.

Chambery Inn New England Road TripChambery Inn New England Road Trip

TripAdvisor offers reviews of the Chambery Inn as well.

We also had an incredible French dinner at Chez Nous Bistro.

Chez Nous French Dinner New England Road Trip

Chez Nous French Dinner New England Road Trip

We had an imaginative lunch where we met the chef at Sloane’s Tavern at the Cranwell Resort.

Sloane’s Tavern Lunch New England Road TripSloane’s Tavern New England Road Trip

Cape Cod

In addition to the Berkshires, Massachusetts offers another awesome experience in Cape Cod where you can have a classic beachfront experience with tons of seafood and exploration.

New England Road Trip

Cape Cod offers something for everyone. For those that love adventure to those that love to kick back and relax.

New England Road Trip

LonelyPlanet gives an excellent summary of the fun that is waiting for you on the Cape.

In addition, TripAdvisor has reviews of hotels and restaurants so you while be in the know.

We checked out the Cape Cod Chamber of Commerce for a bit more info on the city and to help plan where to stay.

Our Cape Cod experience was made perfect by our hotel selection of the Beach Breeze Inn where we got to spend the night in a beach house steps away from the ocean! TripAdvisor has other guests reviews as well.

New England Road TripNew England Road Trip

When we asked around about great dining spots, we found an amazing culinary experience at the Dan’l Webster Inn and savored every bite of of gourmet dining there. Check them out on TripAdvisor.

New England Road TripNew England Road TripNew England Road Trip


During the New England Road Trip, we stopped in Portsmouth and enjoyed the city near the water.

New England Road TripNew England Road Trip

The city is known for its maritime history and you could see examples of it throughout the city.

LonelyPlanet gives a great summary of the area and what to see and do.

When looking for hotels, attractions and dining be sure to read reviews on TripAdvisor.

We redeemed Hilton points to stay at the Hampton Inn Portsmouth Central which was minutes from downtown and the water based attractions.

New England Road Trip

The hotel had a great happy hour with free craft beer and a comfortable room.

New England Road Trip


Our last spot on the New England Road Trip was Newport.

Newport is one of those classic seaside cities loaded with history from 1776.

New England Road Trip

You can explore the area by walking on the bluffs and cliffs which overlook the ocean, giving you incredible views.

New England Road Trip

In addition be sure to check out all the beautiful mansions that line the ocean.

A classic downtown area is great for walking around and doing some shopping as well.

There is so much to do in the area from wineries and breweries to great museums, its an awesome town to visit.

New England Road Trip

Another great resource for a Newport adventure is Discover Newport. You can research activities, hotels and restaurants and plan your adventure.

New England Road Trip

We redeemed Hilton points in Newport and stayed at the Hampton Inn Newport/Middletown.

New England Road Trip

The hotel is recently remodeled and offers a beautiful lobby to relax and enjoy a great breakfast.

New England Road Trip

Road Trip

Our New England Road Trip was a fun adventure.

We visited six states and traveled nearly 745 miles over the few days.

New England Road Trip

Each of the places we visited were amazing, and you could spend several days in each city.

New England Road Trip

We definitely want to return in the future for longer experiences in each area!

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Trip Report

The New England Road Trip is a multi-article trip review highlighting our experience along the way.

The following experiences are included in this trip report:

Note: I was connected with 1Berkshire, Cape Cod Chamber of Commerce and Discover Newport who assisted in arranging some of the experiences during the trip. The views expressed in this multi-article trip report are my own. 

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