New England Road Trip: Experience Mountains, Beaches & Historic Communities

Ultimate New England Road Trip

Six states, 71,991 square miles, and over 14 million people make up the northeast region of the United States known as New England. All of the states are relatively close together, making them the perfect road trip destination. Connecticut, Rhode Island, Massachusetts, New Hampshire, and Vermont were part of the original 13 colonies (Maine separated from Mass later), and are renowned for their beautiful fall foliage, stunning seascapes, towering mountains, and unique regional cuisine. Read on to find out where the best places to visit on your New England road trip are located, and what to expect when you get there.

The Major Cities of New England

Cities to visit on your road trip

New England is centralized by the city of Boston, which serves as the hub for the six states, but has several other major cities and destinations. In Connecticut, the capital of Hartford is in the epicenter of the state, while interesting architecture and the famous Yale University can be found further south in New Haven. Further along I-95, you’ll find Providence, which has excellent Italian restaurants, fascinating animals at the Roger Williams Zoo, and a Dunkin’ Donuts on every corner. To the south, Newport, Rhode Island is home to some of the most beautiful mansions in the world. Many of these mansions belonged to well known wealthy families like the Vanderbilts, Rockefellers, and the Astors. To the east, the former whaling capital of the world, New Bedford, has deep historical roots and preserved cobblestone roads.

Further north are the I-90 cities of Worcester and Springfield, with Vermont’s mountain city of Rutland to the north. Burlington, Vermont is the largest city in the state and offers gorgeous views of Lake Champlain. New Hampshire’s cities are relatively small but do have Manchester and Portsmouth to the south. Maine’s Portland is an old-style city with charming shops, churches, and incredible views of the seaport.

Lighthouses of New England

Visit the historical lighthouse treasures on the coastline

Lighthouses, both active and inactive, dot the shoreline of New England from the New York-Connecticut border all the way to the Maine-Canada border. Each state, including the brief shoreline of New Hampshire, has exceptional views of lighthouses on the coast, and sometimes along the craggy shoals. These old structures provide a glimpse of a time gone by when the coastline wasn’t as developed as it currently is, sophisticated navigational aids did not exist, and when shipping via boat was the only option. Some of the more famous lighthouses in New England are Highland or Cape Cod Light in Truro, MA, Minot Light in Scituate, MA, Boston Light in the harbor of the capital city, Portland Head Lighthouse in Maine, and the often-photographed West Quoddy Head Lighthouse near the Canadian border.

Different Seasons of New England

Four distinct seasons shape New England’s personality

The seasons are what drive New England and set it apart from much of the rest of the country. Unlike anywhere else in the country, the northeast experiences four distinct seasons, with rough, snowy winters, mild, rainy springs, scorching hot and humid summers, and dry, colorful autumns. The constant change is what makes the area so unique, and each season has its own set of activities and events to embrace the ushering in of the time of year. Fall festivals, summer fireworks, spring cleanups, and winter skiing will give you an idea of what makes New England home to over 7 million people.

Islands of New England

Islands large and small off the NE coast

Thousands of islands are located just offshore of every state, Vermont included, in New England. Some you’ve probably heard of, like Martha’s Vineyard, Nantucket, and Block Island, but the area has many equally impressive destinations to choose from like Monomoy Island, Plum Island, and Isle au Haut. Here’s a list of some of the premier island destinations:

Islands of New England

Thimble Islands

Cruise along the Thimble Islands of Connecticut aboard Captain Bob’s tours and private charters!

Block Island

Rhode Island’s most famous island, filled with giant bluffs and sandy beaches.


One of the most pristine and protected areas of Massachusetts, Nantucket is a giant tourist destination for MA residents and international tourists.

Martha’s Vineyard

Find charming villages, lighthouses, sand, and surf at Martha’s Vineyard, located south of Wood’s Hole, MA.

Monomoy Island

Monomoy Island is located south of Chatham, MA, and has no human inhabitants. It is, however, home to migrating birds and gray seals.

Plum Island

On the north shore of Massachusetts near the New Hampshire border is Plum Island. Lighthouses, restaurants, and the wide expanses of salt marshes are subject to occasional visits by migrating Snowy Owls and the Piping Plover.

Boston Harbor Islands

It’s a National Park designated area consisting of many small islands containing lighthouses, old historic forts, and beautiful views of the city.

Mount Desert Island

Mount Desert Island contains the amazing sites of Acadia National Park.

Isle au Haut

Right outside of Isle au Haut is Acadia National Park, both of which are on scenic Penobscot Bay.

Monhegan Island

Halfway up the coast of Maine is Monhegan Island, ten miles from the coast, and only accessible via boat.

Food of New England

A best-of list of regional cuisine from the six states

So what’s the food like in New England? It’s one of the most eclectic places for influence, yet the original food of the area still holds its integrity. Favorite foods also vary by state, even though they are all very close. Connecticut and Rhode Island have favorites like johnnycakes, Del’s Lemonade, clam bakes, and coffee milk (that’s coffee syrup stirred into milk). In Massachusetts, there’s a strong seafood influence, with famous Ipswich clams, local Cod from the Cape, and truly “American” food that you would picture at Thanksgiving feasts like cranberries and turkey. North in Vermont and New Hampshire, food becomes more dependent on cheese, dairy, and maple syrup with local cheese shops, maple syrup farms, and fresh locally grown produce. To the east, Maine has the best lobster in the country, along with the best blueberries and maybe even potatoes.

If you’re in the area for a short time, you may want to try lobster, clam chowder, maple syrup-based bakery items, and a traditional New England breakfast. It’s what they do best.


What to See in Connecticut

Seaside towns, wine trails, museums and activities in the Constitution State

Connecticut is an eclectic state offering entirely different activities and sites in each portion of the state. The coastline offers beautiful beaches, cities, and lighthouses, while just inland lies the Connecticut wine country trail. Further north, the town of Waterbury is nestled into the hills, surrounded by quaint New England villages. Hartford is the state’s commercial and historical center, right on the Connecticut River, with renowned art museums and famous Nook Farm, former homes of Mark Twain and Harriet Beecher Stowe. Here are some other must-see attractions on your road trip route:

Connecticut Visitors Guide

Southford Falls State Park

Beautiful cascading falls in the forest scenery of Southford Falls State Park.

Ocean Beach Park in New London

Often named the best beach in Connecticut, this is right off of I-95, an easy drive from Mystic. Beautiful white sandy beaches and activities make this a must-visit.

Mystic, Connecticut

Mystic is perfectly preserved, complete with bayside lighthouse, standing tall ships, and the museums to browse.

Wadsworth Atheneum

The country’s first public art museum, with artworks dating back thousands of years. Specializing in American artwork, but not limited to it, this museum is located in downtown Hartford.

Connecticut Wine Trail

Over a dozen wineries can be visited along Connecticut’s wine trail, a great experience for any wine lover or novice.

Mystic, Connecticut: A Fast Drive Through Town

Watch this video to get a quick tour of the town of Mystic

Unlike anything else in New England, except for parts of Plymouth, MA, Mystic preserves the original maritime history of this small port on the southeastern coast of Connecticut. This video will give you a good idea of what to expect in this interesting town along the Rhode Island border:

Rhode Island

What to See in Rhode Island

Sightseeing destinations and things to do in the Ocean State

Rhode Island Visitors Guide


Newport might just be the nicest place in New England along the coast. The striking rocky cliffs are decorated with mansions, old and new, along Bellevue Drive and Ocean Drive (a trip you’ll never forget).

Roger Williams Zoo

Roger Williams Zoo in Providence has an eclectic range of animal species, all kept within a relatively small distance. This makes the zoo easy to visit in just a half-day or less (come early on the weekends especially, however).

Sakonnet Vineyards

Sakonnet Point, opposite Newport, is located in Little Compton Rhode Island. A leisurely drive down this peninsula will lead to this remote winery offering wines grown right on the coast, an unexpected treat in this part of New England.

Rhode Island Beaches

Rhode Island isn’t renowned for its beaches, but that’s because they’re a well-kept secret. The secret’s out now, they’re some of the best in New England.

Jamestown Rhode Island (Conanicut Island)

The small island of Conanicut is west of Newport, linked by the famous Newport Bridge. It’s small, but rural and untouched, with grazing sheep, a small village center, lighthouses, windmills, parks, and views of the city across the Narragansett Bay.

Federal Hill

Federal Hill boasts some of the best Italian restaurants in the northeast, gallery shopping, and nightlife in downtown Providence.

Brenton Point State Park

Brenton Point State Park defines Rhode Island and Newport. It’s the tip of Narragansett Bay, always a bit cooler than the mainland, and just minutes from downtown Newport. Stop and watch the boats drift by, bring a kite to fly on the windy rocks, or search around for marine life in the tidal pools that the crashing waves leave behind daily.

Block Island

To the west of Martha’s Vineyard, east of Long Island lies Block Island. High cliffs and inaccessibility preserve its uniqueness and Rhode Island charm. The island can be reached by ferry, but should be booked far in advance during the summer.

Blackstone River Bikeway

The Blackstone River Valley is experiencing a big resurgence and a massive undertaking in the form of the newly constructed Blackstone River Bikeway. This beautiful area winds through hills, rivers, small towns, and connects the 2nd and 3rd largest cities of New England, Worcester, and Providence. 10 miles of the path are complete, and construction is ongoing.

The Newport Mansions of Rhode Island

A video of the famous historical buildings of the Victorian era

Rhode Island has preserved all of the mansions in Newport Rhode Island that have been donated to the Historical Society, as you can see in this video. What’s interesting is that many of the mansions are still in use by wealthy families in Newport to this day.


What to See in Massachusetts

Beach destinations, historic buildings, and offshore islands in MA

Massachusetts will take you across the winding backroads of the Berkshires, down to the rolling dunes of Cape Cod, and up to the rocky shores of Rockport all within a few hours drive of each other. The state has great charm and historical significance. The roots of America are planted deeply into towns like Lexington, Concord, and Plymouth, while the capitol of Boston serves as the financial hub of all of New England and the state of Massachusetts.

Massachusetts Visitors Guide


Travel to the economic, social, and cultural center of New England to experience the museums, islands, villages, and libraries this world-renowned city has to offer. Boston is the commercial hub of New England, and also an incredible city that you can’t leave out of your trip. Fenway Park, Copley Square, The Boston Harbor Islands, The North End, Long Wharf… these are all things that exude New England, and they’re cultural icons of the region.

Quabbin Reservoir

This area is set aside as a giant drinking water supply for Massachusetts, serving over 2 million people, but also has incredible hiking around the reservoir.

Cape Cod and the Islands

Cape Cod is the key attraction of Massachusetts, with millions heading to the island-like peninsula every year. Starting with Bourne and ending in Provincetown, every town has its own charm. This page will give you some of the ten best places to visit on the Cape. As of the minute you cross into Massachusetts on your road trip, start calling Cape Cod just “the Cape.” Otherwise, you’ll stick out like a sore thumb. This video points out some of the finer points of the Cape and Islands. You’ll first be greeted by the Cape Cod Canal and the Railroad Bridge just before entering the town of Bourne. The trip to the end of the Cape takes roughly 90 minutes – 2 hours in no traffic.

The South Shore of Massachusetts

The South Shore, that is, towns south of Boston and north of Cape Cod, offers beautiful beaches in Nantasket, Duxbury, and Plymouth. Follow Route 3A to stay along the coastal towns, and visit favorites like Marshfield, Scituate, Hingham, and Cohasset.


This seaside village on the coast of Cape Anne is an artist’s colony and fisherman’s town, with beautiful aged buildings, restaurants, and lighthouses on the rocky shore.

The Berkshires

Mountainside towns like Lenox, Lee, and Williamstown make the Berkshires an interesting road trip destination in Massachusetts, with historic museums, rolling hills, and colorful mountains.

My personal favorite spot in Massachusetts: The unspoiled beaches of Cape Cod are some of the best in the country. Towns like Chatham, Harwich, and the shoreside villages of Nauset give the greatest example of “cape life.”

New Hampshire

What to See in New Hampshire

Mountain lakes, deep forests, and scenic backroad highways make a great road trip in New Hampshire.

New Hampshire Visitors Guide


Home to the famous bike week of New Hampshire, Laconia’s atmosphere feeds off the beautiful Lake Winnipesaukee nearby.

North Conway

Sitting at the base of Mount Washington Valley, North Conway is known for its unique shops, splendid views, and year-round appeal for skiing, dining, and shopping.

Franconia Notch State Park

Perhaps the most beautiful area of New Hampshire is Franconia Notch State Park. This area was once the home of the Man on the Mountain (an oddly shaped rocky face which resembled an old man’s face), which has since crumbled. However, the mountain views are still some of the best in the country and not to be missed.


Portsmouth has a small but beautiful shoreline with historic boats, shoals, and the often-photographed Cape Neddick Lighthouse.

Mount Sunapee Region

This region of New Hampshire is known for its easily accessible ski resort and crystal clear Lake Sunapee.


What to See in Maine

Maine’s spectacular seashore, including Acadia National Park and Portland.

Maine Visitors Guide


Portland is one of the best cities in America, according to many surveys, to live and to visit. With unique restaurants, an easygoing attitude, and incredible marine scenery, the city is located on the cold waters of Casco Bay.

Acadia National Park

Acadia, located on Mount Desert Island, is the most visited natural scenic destination within the state. The rugged coastline offers unmatched views of the crashing Atlantic waves, while the original carriage roads of the park have been preserved to hike and bike.

The Maine Coast

The Maine coast has some of the most photographed towns in the USA, like Bath, Rockland, and Bar Harbor, which will be understood once you visit these shore communities.


Further inland is the state capitol, Bangor, which is the hub of northern Maine and lies on the Penobscot River.


Kittery is the first town over the New Hampshire border and known for its hundreds of shopping outlets and stores.

Quoddy Head State Park

Quoddy Head is located on the Canada-U.S. border and is best known for its red and white striped lighthouse, West Quoddy Head Light. The park also has miles of forest and hiking trails to enjoy and explore.


What to See in Vermont

The Green Mountains, rolling farms, and small towns in Vermont

Vermont is the northwestern-most state in New England, directly adjacent to New York and New Hampshire. The state is known for the Green Mountains, a region on the western stretch of the state that contains unmatched farmland scenery. To the north lies Lake Champlain, one of the largest bodies of freshwater in the United States, and the largest city, Burlington. To the south, Route 12 is one of the best sightseeing paths to take in the entire state, winding up and down mountains, weaving into small towns, farms, and alongside creeks and waterfalls. Each section of the state is very distinct, but they all share the same rustic appeal that makes the state so interesting.

Vermont Visitors Guide

The Green Mountains

Part of the Appalachian mountain range expanse, the Green Mountains are how the state got its name. Translated from French, Verts Monts is “green mountains.”


It’s not the home of the famous 60’s festival, it’s a small community on Route 4 in the middle of the state, often named the most beautiful in the country.


Stowe is one of the premier ski getaways in the state, nestled between Mount Mansfield and the Green Mountains. It has some excellent spas, some of the best-reviewed restaurants in New England, and gorgeous views.

Lake Champlain

Lake Champlain is located on the Vermont-New York border, home to an underwater ancient reef, and actually runs partially into Canadian territory. The massive lake stretches over nearly half the western border of the state. The city of Burlington is located right on the shore of the lake.


The beautiful town of Montpelier is the state capitol, but also a quaint town enveloped by mountains, rivers, and forests. Characteristic of the state, the Capitol Building is set in a rural setting, surrounded by blooming flowers and a booming tourist scene in the summer.

Route 100

If you only have time to visit one area of Vermont, visit the scenic Route 100. This road trip favorite winds from north to south (or vice versa) through much of the state, including the Ben and Jerry’s Ice Cream Factory in Waterbury, Stowe Recreation Path, and countless villages, stores, and churches. The road is particularly well-traveled in the autumn months when foliage is at its peak.


Where to Stay in New England

Places to stay and how to find them

New England is best seen by car, and on your road travels, you’ll come across the big chain hotels as well as some small bed and breakfasts and inns. Use your own judgment, along with to tell you where the best places might be. Most people prefer to experience New England for what it is, and you can’t really get that feeling by staying at some of the bigger chain hotels. There are some exceptions where the big chains have acquired historical buildings, but for the most part, the best places are those small B&B’s, inns, and cottages.

More Travel Destinations in the United States

Road trips, National Parks, cities, and accommodations across America

Plan out your trip with these guides on some of America’s best travel destinations. The following page is an index for all of my guides for U.S. destinations, including Yosemite, Death Valley, Washington DC, and other destinations across the country.

Travel Destinations in the USA

Hundreds of National Parks, spanning coast to coast, world-class cities, and charismatic small towns in between rural farmlands. It’s what makes the United States such a unique world travel destination, begging to be explored. From the coastal inlets…


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