Skip to main content
Castle Hill Inn

Contrasts of New England: Your 13 Day New England Travel Itinerary

13 Days, 12 Nights

New England covers six states: Connecticut, Rhode Island, Massachusetts, New Hampshire, Maine, and Vermont. Hundreds of miles of Atlantic coastline range from rocky shores to long sandy beaches. Inland, there are impressive mountain ranges, a peaceful agricultural landscape and dozens of unspoiled lakes. The contrasts are everywhere. From America's most attractive cities to small picture-perfect villages complete with picket fences, village greens, and clapboard homes. In New England you have the opportunity to explore great cultural activities and gems as well as enjoy the relaxation of the outdoors.

We designed this self driving tour itinerary with suggestions on how you can experience the diverse nature of the region. If the idea of driving to a different place to stay each night doesn't appeal to you, we've got a plan that allows you to explore the region at a leisurely pace.

Day One: Boston, Massachusetts to the Southern Maine Coast

Boston Syline
Boston Sunset | walknboston via flick / CC BY 2.0

Note: if this is your first visit, we recommend at least a three night stay in Boston. For the repeat visitor, there are plenty of favorite spots to revisit. Spend a few nights to reacquaint yourself with the city of Beantown! If your travels have you arriving at Boston Logan Airport in the late afternoon or early evening, we recommend staying the night in the city. If you arrive in the early afternoon, you could head straight from the airport to your first stop. There are a variety of ways to get into the center of Boston, including public bus, subway and taxi. If you're ready to begin your New England journey, prepare for an approximately 1-1/2 hour drive north to the  Ogunquit, ME area. This area provides an excellent base for you to explore the southern Maine and New Hampshire coastline. Places to stay in Boston Places to stay in Southern Maine

Day Two: Exploring the Southern Maine Coast

On your first full day in Maine, explore The Kennebunks where the politically prominent Bush family calls home in the summer months. For a leisurely way to see the sights head over to the Seashore Trolley Museum, where you can take a beautiful four mile ride to enjoy the local history. Looking for some sand and sunshine? Nearby Ogunquit is the perfect seaside holiday destination with long sandy beaches, and abundant with activities like the increasingly popular sea kayaking and paddle boarding. A 'must see' is Perkins Cove, where you can take a scenic boat tour to fully experience the beautiful Maine coastline. Places to stay in Southern Maine

Day Three: Exploring the Central Maine Coast

Portland, Maine
Portland, Maine Lighthouse | Jeff Gunn via flickr / CC BY 2.0

Spend the day exploring the coastline further north. An easy hour drive will bring you to Portland, ME. Set on Casco Bay, this busy and historic city offers great shopping, dining, and art museums. Portland is the perfect place to go on a whale watch or take the ferry service to the nearby island communities. Freeport, ME offers wonderful designer outlet shops in a New England village setting, just 20 minutes from Portland. Time allowing (the drive is nearly another 2 hours one-way) head to Camden, ME , a lovely old seaport. While you're there, you have the chance to stay at one of their many luxury B&B's,  take a cruise on one of the old wooden schooners, or climb Mount Battie overlooking the Bay. Places to stay in Central Maine

Day Four: Southern Maine Coast Whale Watch Trip

Take a whale watch trip today. There are plenty of reputable companies that offer whale watching trips from both the Ogunquit or Kennebunk area. Ask your innkeeper for recommendations. Places To stay on the Southern Maine 

Day Five: White Mountains of New Hampshire to the Green Mountains of Vermont

White Mountain National Forest
White Mountain National Forest | A. Duarte via flickr / CC BY-SA 2.0

Today, drive westwards through the White Mountains of New Hampshire and into Vermont. Traveling from the southern Maine coast to Vermont is a fairly long drive (approximately four hours) as the roads are not major highways and traffic can be slow. However, the journey is a beautiful one. It will take you through some wonderful mountain scenery and some of New England's prettiest villages. We suggest that you skip the main interstate highways, and instead head westwards along Rte 302 and through North Conway, NH (a great place to stop for tax free outlet shopping!). Continue your drive through the White Mountains Presidential range, then head west into Vermont. We suggest you base yourself here for at least four nights to enjoy the bucolic beauty of the Green Mountains. Places to Stay in Vermont

Day Six: Exploring Northern Vermont - Montpelier and Stowe

Spend the day exploring the northern counties of Vermont and visit Montpelier, the smallest state capital in the country with only 8,000 inhabitants. Montpelier has a lively atmosphere and its two main roads, State Street and Main Street, are dominated by fine coffee houses and unique boutiques. Make sure to stop in for a quick tour of the gold domed state house and fit in a visit to the local historical society. Continue on to the famous Ben & Jerry's Ice Cream Factory in Waterbury, VT to take a lively tour of New England's most famous ice cream brand, complete with a sample at the end! From Waterbury, visit Stowe, VT, known as the Ski Capital of the East. This lively and welcoming resort town has appeal in the summer, fall, and winter. For the more adventurous visitors, a five-and-half-mile recreation path is available for biking or walking. However, for a more leisurely tour, you can take a gondola on Mount Mansfield (the highest peak in Vermont) and see the magnificent view from its peak. On a clear day you can see the Adirondacks in New York state, the Laurentians in Quebec, and the White Mountains in New Hampshire. Places to stay in Northern Vermont

Day Seven: Exploring Burlington and the Lake Champlain Region

Church Street, Burlington
Church Street, Burlington | Ryan Scullin via flickr / CC BY-ND 2.0

Discover Burlington, VT and Lake Champlain. Burlington, the largest city in Vermont, is nestled on Lake Champlain,  one of the largest freshwater lakes in the United States. A large university town with a great college atmosphere and gentle hum, downtown Burlington is home to unique Vermont craft shops, delicious restaurants, and a pedestrian-friendly Church Street that runs through the main downtown shopping district. While in town, visit the Shelburne Museum, where you will find a collection of over 400 years of Americana, from quilts to toys, tools and art. Also well worth a visit is Shelburne Farms, a 1400-acre working farm, national historic site and nonprofit environmental education center located on the shores of Lake Champlain. Places to stay in Northern Vermont

Day Eight: Exploring Vermont's Northeast Kingdom

Today take the time to explore a unique corner of northern New England and visit Vermont's Northeast Kingdom. Remote, rugged, and unspoiled, there are many great outdoor recreational opportunities as well as covered bridges, historical districts, lakes, and charming villages. St. Johnsbury, VT is the largest town where you can visit the Fairbanks Museum, tour the Maple Grove Farms Maple Museum and Factory, or head to Derby Line where you will find half the local opera house in Quebec and the other half in Vermont! Places to stay in Northern Vermont

Day Nine: Vermont to the Connecticut Hills

Historic Deerfield
Historic Deerfield | Massachusetts Office of Travel & Tourism via flickr / CC BY-ND 2.0

 Today you head south through the Green Mountains of Vermont and to another beautiful stop in New England: Western Connecticut. En route and well worth a visit is Historic Deerfield Village. Situated on a 330-year-old, mile long street, Historic Deerfield preserves and interprets the architecture and lifestyle of a prosperous early New England town. The extraordinary homes with antique furnishings, along with exhibition galleries and collections are some of the finest examples of Americana in the United States. Places to stay in Connecticut

Day Ten: Exploring the Litchfield Hills, Connecticut

A favorite for many affluent New Yorkers and celebrities, the Litchfield Hills are an easy retreat for many who want to escape the hustle and bustle of the big city. Litchfield, CT has an impressive village green lined with grand homes plus excellent restaurants, antique shops and art galleries. There are wonderful outdoor activities throughout the area to enjoy too such as golf, fishing, canoeing, biking and great variety of wonderful nature centers. Places to stay in Connecticut

Day Eleven: Exploring the Connecticut River Valley Region

Today journey into Hartford, Connecticut's capital city. Apart from its impressive Old State House and America's oldest State Capitol, the main magnets are the homes of two influential 19th century writers: Mark Twain (The Adventures of Tom Sawyer) and Harriet Beecher Stowe (Uncle Tom's Cabin). Take a tour and understand more about the lives of these fine writers whose writings are still favorites. Next continue southwards through the CT River Valley area and visit some of the area's great attractions such as the Essex Steam Train and Riverboat Ride. Or visit the Goodspeed Opera House, famous for its nationally acclaimed productions. Places to stay in Connecticut

Day Twelve: Exploring the Berkshires

Norman Rockwell Museum
Norman Rockwell Museum | Massachusetts Office of Travel & Tourism via flickr / CC BY-ND 2.0

From your western Connecticut base you are also within easy driving distance (approximately one and half hours) to the The Berkshires. Drive north today and visit the Norman Rockwell Museum. Norman Rockwell is one of America's greatest popular artists, as he painted pictures illustrating some of his deepest concerns and interests, including civil rights, America's war on poverty and the exploration of space. The museum is a wonderful tribute to his work and artistic legacy. The Berkshires are also a wonderful arts and cultural venue and the summertime especially brings some exceptional events to the region as the Boston Symphony relocates and performs. Places to stay in The Berkshires

Day Thirteen: Depart Boston or New York City

From your base in Western Connecticut you are in easy proximity to the international gateway cities of New York, Newark (NJ) or Boston. Depart today from one of these gateways or take the time to enjoy a couple of nights in the city before departure. Places to stay in Boston