Travel
Your New England Summer Road Trip Itinerary
September 27, 2018
0
, , , , , , , , ,

Breeze through significant historical sites, natural delights and creative highlights of America’s northeast with this 8-day New England summer road trip itinerary.  This route will take you to five states – Massachusetts, New Hampshire, Maine (just), Rhode Island, Connecticut – with a sixth, New York, depending on your choice of airports and the optional detour.

NOTE: We trialled and travelled this itinerary in seven days and it’s possible but high speed. I’ve made some tweaks and added a day to give it a more comfortable pace. Of course, it will depend on how many of the sights and activities you decide to include.

Full Disclosure: I may earn compensation for my endorsement, recommendation, testimonial, and/or link to any products or services from this website at no extra cost to you. I only recommend products/services that I use and love, therefore feel comfortable recommending.

Day 1

Arrive in Boston and check into your accommodation, ideally a centrally located downtown near Faneuil Hall. Put on some comfy walking shoes and make your way to the Visitors Center at Faneuil Hall. From here we will take the north arm of the Freedom Trail. If you’re hungry, grab some food at the Marketplace before following the red line around some of Boston’s most important and interesting historic sites including Paul Revere House and Bunker Hill. Once you reach the far north end of the trail at Bunker Hill, make your way back again. I recommend stopping in North End on your return journey to sample Little Italy’s finest for dinner (scroll to the end of the post for food recommendations).

Driving distance:  Local driving distance depends on accommodation location and chosen activities.

Boston historic sights and architecture
Boston historic sights and architecture
Historic Boston architecture
Old State House, Boston
Faneuil Hall, Boston
Faneuil Hall
Delectable delii sandwiches at Monica's Mercato
Delectable delii sandwiches at Monica's Mercato

Day 2

Spend the morning tackling the southern portion of the Freedom Trail, ending in Boston Common. From here I recommend making an extra 20-minute walk to Copely Square for the incredible architecture of Boston Public Library and Trinity Church. Find some lunch in this area before grabbing an Uber or taking a train/bus to the Museum of Fine Arts, Boston.

Alternatively, skip the architecture and make your way to Boston’s pop culture icon – the bar that inspired the television show Cheers! You will probably have to make a booking at the former Bull & Finch at 84 Beacon St, now known as Cheers The Original – because there is a replica at Faneuil Hall.

Depending on your interests I suggest continuing your art education a 6-minute walkaway at the Isabella Stewart Gardner Museum, or visiting sports fans might prefer walking 10-minutes to Fenway Park, home of the Boston Red Sox. Alternatively, ride back into town and explore the Boston Tea Party Ships and Museum.

Driving distance:  Local driving distance depends on accommodation location and chosen activities.

Art Highlights of Boston and Beyond
Museum of Fine Arts, Boston
The beautiful courtyard of the Gardner Museum
The courtyard of the Isabella Stewart Garnder Museum
The Raphael Room
The Raphael Room at the Gardner Museum
Boston Tea Party Museum
Boston Tea Party Museum

Day 3

Pick up your rental car first thing and head north to Salem. Here visit the House of Seven Gables, drive down Chestnut St and learn about Salem’s infamous witch trials at the Salem Witch Museum. Depending on your interests, you could spend an entire day exploring historic Salem sights. However, for the timeline we have set ourselves, this will give you a good taste of the town, it’s history and significance.

From Salem, drive to Rockport for shopping and lunch in the arty, seaside town. Then continue north to Portsmouth, New Hampshire. You may choose to stay here the night, or continue another 15-minute drive north over the Maine border to the smaller and more affordable accommodation in scenic York.

Driving distance:

Boston to Salem MA 36km (approx. 22mi), 40mins. 

Salem to Rockport MA 37km (approx. 23mi), 40mins.

Rockport to Portsmouth MA 95km (approx. 59mi), 4hr 5mins.

Salem Witch Museum
Salem Witch Museum
Garden views from the House of Seven Gables, Salem MA
Garden views from the House of Seven Gables
Ye Old Pepper Companie
Apparently America's oldest candy company
Nautical vibes in Rockport
Nautical vibes in Rockport

Day 4

Spend the morning exploring the historic center of Portsmouth. If you found yourself in York, Maine, go for a morning coastal walk before returning to Portsmouth.

Drive to Plymouth and let the helpful people at the Visitors Information Center (cnr Water St and Memorial Dr) chart you a walking trail of the town’s most significant historic sights including of course, Plymouth Rock. Spend the night in Plymouth.

Driving distance: Portsmouth NH to Plymouth MA 188km (approx. 117mi), 2hrs. 

Governor John Langdon House, Portsmouth NH
Governor John Langdon House, Portsmouth NH
Plymouth Rock
Plymouth Rock
Plymouth weather vane
Plymouth weather vane
Plymouth Rock
Plymouth Rock lies within this neoclassical structure

Day 5

Start early and drive to Newport, Rhode Island. Have breakfast in the historic downtown and see the impressive boats at Bannister’s Wharf. The wharf is buzzing with wealthy mariners and tourists on a summer’s day, so thought it offers shopping and restaurants, they are at the expected heightened prices.

Take a drive down Bellevue Avenue and observe imposing Newport Mansions of the gilded-era. Stop in for a tour of at least one.  The mansions include the former Vanderbilt family summer home – The Breakers – found on Ochre Point Avenue, not far off Bellevue.

Continue driving to Mystic for the evening.

 Driving distance:

Plymouth MA to Newport RI 98km (approx. 61mi), 1hr 20mins. 

Newport RI to Mystic CT 78km (approx. 48mi), 1hr 5mins.

Bannister's Wharf, Newport RI
Bannister's Wharf, Newport RI
Former Vanderbilt summer residence - The Breakers
Former Vanderbilt summer residence - The Breakers
The Elms, Newport Ri
The Elms, once summer home of coal baron Edward Julius Berwind
Rosecliff commissioned by Commissioned by Nevada silver heiress Theresa Fair Oelrichs in 1899
Rosecliff commissioned by Commissioned by Nevada silver heiress Theresa Fair Oelrichs in 1899

Day 6

Spend the morning sightseeing in and around Mystic, Connecticut. You might spy the Mayflower II, which is undergoing restoration at Mystic Seaport in preparation for the 2020, 400th anniversary of the Pilgrims’ landing at Plymouth.

After lunch, drive to Stockbridge, Massachusetts.

Driving distance:  Mystic CT to Stockbridge MA 204km (approx. 48mi) 1hr 5mins.

Mystic Seaport Museum, Mystic CT
Mystic Seaport Museum
Mystic CT
Mystic CT
Mystic weather vane
Mystic weather vane

Day 7

Spend a day exploring The Berkshires with these ideas:

Driving distance:  Local driving distance depends on accommodation location and chosen activities.

Norman Rockwell Museum
Norman Rockwell Museum
Main Street of Stockbridge
Main Street of Stockbridge illustrated by Norman Rockwell
Views of The Berkshires landscape from the Norman Rockwell Museum
Views of The Berkshires landscape from the Norman Rockwell Museum
Historic building in Great Barrington
Historic building in Great Barrington

Day 8

From here you may choose to return to Boston Logan Airport for your flight out, or a little further to Newark Airport in New Jersey. If you do choose to exit via Newark, may I suggest a detour?

Bethel Woods Center for the Arts, in Bethel, NY, is located on the original 1969 site of the world-famous Woodstock music festival. The property is now a live music venue, arts education campus and has a museum documenting and preserving the magic and misery of Woodstock. If you are a music fan, I thoroughly recommend a detour to Bethel to see the site and museum.

Driving distance: Stockbridge to Boston MA 210km (approx. 131mi), 2hrs 10mins.

Stockbridge MA direct to Newark NJ 283km (approx. 176mi), 2hrs 45mins.

Stockbridge MA to Bethel NY 237km (approx. 147mi), 2hrs 32mins.

Bethel NY to Newark NJ 178km (approx. 111mi), 2hrs.

The site of 1969 music festival, Woodstock
The site of 1969 music festival, Woodstock
Woodstock Bus
Woodstock Site - National Register of Historic Places

Places to eat, drink and be merry

Boston

Equal Exchange Café (coffee)

Southend Buttery (brunch)

Monica’s Mercato (sandwiches)

Carmelina’s (dinner)

Bostonia Public House (dinner)

Mike’s Pastry (dessert)

Other New England favourites

Derby Joe, Salem MA (coffee and sandwiches)

The Lobster Pool, Rockport MA (lunch)

Clay Hill Farm, Cape Neddick ME (dinner)

Bob’s Clam Hut, Kittery ME (lunch)

Lobster Hut, Plymouth MA (lunch or dinner)

Scratch Kitchen, Newport RI (breakfast or lunch)

Meg’s Milk Bar, Newport RI (brunch and coffee)

S&P Oyster Co., Mystic CT (dinner)

Red Lion Inn, Stockbridge MA (dinner)

Bethel Market Café, Bethel NY (lunch)

Fisherman's Platter for two and garden salad at Lobster Hut, Plymouth
Fisherman's Platter for two and garden salad at Lobster Hut, Plymouth
Lobster Rolls at Lobster Pool, Rockport
Lobster Rolls at Lobster Pool, Rockport

Soulful souvenir ideas

As I was moving around New England, I kept an eye on locally made products and stores with unique souvenirs. My top picks are:

Ready to plan your New England road trip?

Find flights to Boston with Skyscanner.

Search for accommodation using Tripadvisor.

Rent a car for your New England road trip with National Car Rental.

Don’t forget travel insurance, I recommend Seven Corners or World Nomads.

Use this guide to tailor yourself a fabulous New England summer road trip. If you have an extra day, I would suggest splitting it between Boston and Salem. Spend the night in Salem or Rockport and continue to Portsmouth the following day.

Have feedback or questions to share?  Please drop them in the comments below.

Peace, love and inspiring travel,

Madam ZoZo

Remnants of a New England summer road trip
Your New England Summer Road Trip Itinerary - Massachusetts, New Hampshite, Maine, Connecticut, Rhode Island

About author

Madam ZoZo

Hi! I'm Madam ZoZo, aka Zoë, an Australian designer, creative consultant, blogger and digital nomad. I'm passionate about travel, design, dance and new experiences that fuel my creativity. I strive to travel in a style that is gentle on the earth and that contributes to the communities I visits, even if it is merely to take away a greater understanding of a different culture. Duende by Madam ZoZo, is where I share the stories of my travels and the duende (soul/inspiration) I find along the way.

Manhattan skyline from the Statue of Liberty, New York City

Must See in NYC – The First-Time Visitor’s Guide

Breeze through significant historical sites, natur...

Read more
Creative Corners - What to do in Shanghai, China

Creative Corners – What to do in Shanghai

Breeze through significant historical sites, natur...

Read more
Shwedagon Pagoda, Yangon, Myanmar

Things to Know Before You Go – International Travel Checklist

Breeze through significant historical sites, natur...

Read more

There are 0 comments

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Pin
Share
Tweet