A Local’s Guide to The Ultimate New England Road Trip

A Local's Guide to New England

Why Visit New England?

When I first moved to Rhode Island in New England from the west coast, some of my California friends were very confused about New England. New England is a geographic area comprising the states of Connecticut, Rhode Island, Massachusetts, Maine, New Hampshire, and Vermont. It is in the very northeastern United States and has bustling seaside towns complete with gorgeous lighthouses on its rocky coastline or islands, and quaint ski or artist towns nestled in forested mountains.

Native Americans originally occupied New England until colonists settled here around 1600. Colonial history still abounds in places such as Salem, Massachusetts, Plimoth Plantation, and Newport, Rhode Island. New England was a staging ground in the abolition movement, religious freedom in the burgeoning United States, and the industrial revolution.

Its geography is some of the most diverse in the United States. New England has coastal grasslands, many islands, and a gorgeous mountainous coastline. And in just a week or two, you can explore it on a New England road trip.

One of the highlights of New England, and the reason many people know it, is its astounding, vibrant, and multicolored fall foliage, which can be found throughout the region.

Plan a Trip to Visit New England

Rent a car

Due to the distances you must cover and the relatively rural nature of our northeastern states, really experiencing New England requires a car. Alternatively, you could take a train throughout the area but would have a hard time leaving the cities.

Where to Begin Your New England Road Trip

New England road trip itinerary www.thedailyadventuresofme.com
Driving map made using Google Maps round trip from JFK stopping in Hartford, CT, Mystic, CT, Newport, RI, Cape Cod, MA, Boston, MA, Acadia National Park, ME, Stowe, VT, Springfield, MA.

The largest New England airport is in Boston. You can also fly into any of New York City’s airports and drive about an hour into Connecticut to start your journey.

The New England States

If you click on any state name, it will bring you to a list of all my articles about that state.


things to do in New England
Old Saybrook, Connecticut

There are many shades of Connecticut, from the affluent suburbs of NYC to the rural treed areas of the Eastern state; Connecticut is the inspiration of the Gilmore Girls’ Star’s Hallow.

Planning a New England road trip
Kent Falls State Park

Connecticut Highlights

  • Fairfield County– Affluent suburbs of New York City.
  • Litchfield County– Rural farmland with cute, little villages.
  • Hartford– Connecticut’s capital with a hip waterfront and great hiking nearby at Talcott Mountain. Be sure to visit the Mark Twain House.
  • West Hartford– One of my favorite restaurants anywhere, Restaurant Bricco, is in this shopper and diner’s paradise.
  • Mystic is a Colonial town with an excellent aquarium, a cute downtown, a working drawbridge,  and a Colonial Seaport.
  • Connecticut’s coastline is perfect for kayaking among its grassy marshland, although they are not the best New England Beaches.
  • The Connecticut River winds through most of the state. Take a boat ride down it or explore a few of the towns nestled along its shoreline, like Essex.
  • Wethersfield- Wander along the streets of the oldest town in Connecticut, then enjoy a walk by its waterfront.
New England Road Trip Itinerary
Foliage in Eastern Connecticut

Rhode Island

Itinerary New England Trip
Warwick, Rhode Island

This state is one of my favorites, maybe because it is where I live, but also because even though it is small- just 37 by 48 miles- it has 384 miles of serpentine, rocky coastline. Here are a few of my favorite places to visit. Check out 47 Fabulous Things to Do in Rhode Island.

Things to See in New England
Castle Hill Lighthouse
  • Newport– a historic summer retreat for America’s elite. This coastal town is my favorite, and most of my time is spent exploring this town!
  • Providence– Spend an evening dining in our version of Little Italy, Federal Hill, or catching a spectacular public art exhibit, Waterfire, on our capital city’s canals.
  • Block Island– an easily accessible New England island perfect for beaches, biking, and boating.
  • Westerly- This town has the opulent Ocean House, the casual beaches of Misquamicut, and the stunning natural beauty of the Napa Tree Conservation area.
  • Narragansett has the best flat, white sand beaches in the state.


Most people center their time in Massachusetts in its capital city, Boston, a small bustling city full of US history. But I recommend you head out into its beautiful mountain areas, such as the Berkshires.

How to plan an ideal New England road trip
The Paul Revere Statue Boston with North Church in the background


  • While in Massachusetts, you must visit its capital, Boston, a city of immigrants steeped in colonial history but with a vibrant art, music, and food scene.
  • Salem,- the site of the witchcraft trials of the 1600s and the home of Nathaniel Hawthorne, is one of the most unique of the New England towns.
  • The Berkshires in Western Massachusetts are a perfect spot for camping or taking in an outdoor concert at Tanglewood.
  • While in the Berkshires, be sure to see the Bridge of Flowers in Shelburne.
  • Northampton is one of my favorite Massachusetts towns and is an arty hippy haven.
  • Springfield is the home of the Basketball Hall of Fame, Yankee Candle, a butterfly museum, and The Eric Carle Museum.
  • Visit Massachusetts’s famous islands, such as Nantucket and Martha’s Vineyard.
  • Cape Cod is a peninsula with great bike rides and hikes, fabulous beaches, and seafood.

what to do in New England, USA

New Hampshire

New Hampshire has the most chill New England vibe. It has excellent foliage with its Presidential white mountain range and many laid-back, family-friendly ski towns.

Family hikes in Lincoln New Hampshire www.thedailyadventuresofme.com
Bridge over the Harvard River
  • The White Mountains are part of the Appalachian range and are full of waterfalls, lakes, and ski mountains. They are a perfect place to escape for families or couples. The White Mountains are one of the best places to experience a good New England autumn. Here is a list of my favorite New Hampshire hikes.
  • If you don’t have much time for your road trip, consider this 4-Day New Hampshire fall road trip.
  • Lincoln- one of our yearly haunts, is surrounded by great hiking, skiing, and many family activities.
  • North Conway– Full of shopping, North Conway is a perfect family town oozing New England charm, and near Santa’s Village and Storyland amusement parks.
  • Skiing! Although you can ski in Vermont, New Hampshire, or Maine, Vermont and New Hampshire are where most New Englanders head to ski. We love to ski; even Rhode Island has a tiny ski hill.


One of my favorites, Vermont highlights its artists and locally grown food and is a ski destination. It is the most upscale of the mountainous New England states.

New England trip planning
A sleigh ride in South Woodstock
  • Vermont is an outdoor lover’s paradise. We often go to tennis camp at Sugarbush, where there is also skiing.
  • Ben and Jerry’s Factory– Ice cream is one of my favorite foods, and it is so worth a visit to this factory tour, which includes tastings at the end.
  • Visit the ridiculously charming mountain town of Woodstock, where you can shop and eat and do any number of outdoor activities.
  • Learn all about the local arts scene in Quechee. Read about a weekend in Woodstock and Quechee.
  • Read more about exploring Vermont in A Family Road Trip from Boston to Montreal.
New England itinerary
Downtown Woodstock


Maine is an outdoor-lover’s paradise, and Mainers are a rugged breed. Although the coast is relatively populated, there is plenty of untouched wilderness in this state, which covers half of the landmass of New England.

What to see in New England
Tumbledown Mountsain


  • Maine’s western mountains are a place of supreme peace, not overly populated and full of glorious wilderness.
  • Acadia National Park in Northern Maine is one of the US’ prettiest parks, with wooded forests along Maine’s long coastline. Although it is a long drive to get to, it is a must-see! Please read about my visit to Acadia National Park.
  • The coastal town of Portland is close to Boston and has an incredible food scene, lighthouses, and plenty of coastal outdoor activities. Read 47 Fabulous Things to Do in Portland.
Why visit New England
Sand Beach in Acadia National Park, Maine

When to Visit New England?

There are good reasons to explore New England in any of its distinct seasons.

Summer in New England

If you love the outdoors, summer will allow you to take advantage of all the beaches, lakes, and waterfalls New England offers. Of course, with such perfection can come crowds. If you want to visit our islands, this is an ideal time to visit.

Fall in New England

New England road trip stops
The colorful rocks of Harvard Falls in Lincoln, New Hampshire, during autumn

Although the waters will be too cold to enjoy, there is nowhere in the world with better autumn colors than New England, especially in the northern states. It is the main reason people know about New England and visit. The farther north you travel, the more vibrant the colors are generally. It is tricky to know when the leaves will change, so you may have to change your itinerary to chase the leaves when you come, as they are only in peak for about a week, and the time varies by year.

Spring in New England

This shoulder season has the fewest crowds and the joy of spring flowers and bright green leaves. You won’t be able to lay on the beach, but you can usually still take a bike ride or hike. We may still get snow in spring, and some places won’t be open until after Memorial Day.

Winter in New England

Winter in New England
One of New England’s colonial Bed and Breakfasts, the Cranmore Inn, North Conway, New Hampshire

New England feels so much like Christmas; it is an ideal place to feel winter. Our winters are mild enough that although there is enough snow in our mountains, it is warm enough to enjoy skiing or any winter sport. And, of course, enjoy a hot chocolate by the fire in our cute mountain bed and breakfasts.

This area of the US is one of the best. I hope this article inspires you to plan a trip here. Let me know in the comments if you have any questions or ideas of places that you think I missed.

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4 thoughts on “A Local’s Guide to The Ultimate New England Road Trip”

  1. We sure loved our first visit to New England. But we did not go as far as Connecticut or Rhode Island. Great reasons to plan another road trip in New England. I am sure it would be great it all seasons.

  2. Thank you for explaining the geography of New England. This was something I meant to investigate, but never did. It is the area of the USA about which I know least, although I did drive up from Boston to Vermont and New Hampshire a few years ago for “leaf peeping”. You are so right! The vibrant fall colours are fantastic. Rhode Island sounds like a wonderful place to call home.

  3. I love the idea of a New England road trip out of JFK or Boston! It is the one part of the US I’ve been to as a kid but not really as an adult. I have wanted to check out Rhode Island for a long time: I’d love to see Newport and Block Island. Maine also looks so pretty! I feel like I could so easily spend a month or more there to enjoy the coastline and the wilderness further north and west that you mention.


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