New England and North Eastern USA

The Freedom Trail

The Freedom Trail

14 Nights Boston to Boston 

All six states of this northeastern corner of America are rich in a common heritage and this is reflected in its historical sightseeing. The country inns, antique shops, small towns and covered bridges provide perfect settings for your tour. Enjoy distinctive New England food, especially along its coastline where you will also find artists colonies with galleries, museums and long sandy beaches.

Newport Mansions
Old Sturbridge Village
Plimoth Plantation
Cape Cod
Mount Washington Railway
Acadia National Park
Norman Rockwell Museum

This is just an example itinerary for a Boston and New England fly drive. If you have a different itinerary, schedule or fly drive in mind, please email us for more details or call us on 01892 779900.

Day One & Two - Boston

Boston is yours to discover, combining the old and the new like no other city in America. Put on your walking shoes and explore along the Freedom Trail, a 3-mile walking tour of 16 historic sites from the Colonial and Revolutionary Era. Hop on the famous Old Town Trolley Tour, which brings Boston's history and sights to life while offering an excellent way to traverse the city. Be sure to ride the swanboats in the Public Gardens, shop and eat in Quincy Market, perhaps enjoy a dinner cruise or a dinner overlooking the lights of the city, take the 'T' to visit Harvard Yard and Cambridge where you can shop in the100 stores in the Cambridgeside Galleria, or you could even take a whale watch cruise from Boston's spectacular Aquarium. Boston's numerous museums and art galleries are also available to you. Experience and enjoy the friendly welcome for which the people of Boston are well known.
Stay 2 nights.

Day Three - Portland (111 miles)

Travel along the north shore of Massachusetts to Salem - best known for one of the most notorious periods in American history when, in 1692 hundreds of men, women and children had their neighbours put on trial as practising witches and wizards. Whatever the true cause of the accusations the one certain thing is that the phenomenon has become a cottage industry here and is now a home for many psychics. Salem also has its own Heritage Trail that takes you to museums and the Witch House where pre-trial investigations took place. You should also plan a stop in Kittery, where you will find more than 100 factory outlet stores including big names such as Calvin Klein and Brooks Brothers. Visit the summer communities of Kennebunk and Kennebunkport, seasonal home to former US President George Bush, and boasting many fine restaurants. Tonight you will be in Portland, an historic port city where visitors are drawn to its restored Old Port Exchange area on the waterfront with its many restaurants.
Stay 1 night.

Day Four & Five - Bar Harbor (174 miles)

Head north to Freeport to explore some of New England's best factory outlet shopping. Continue on and lunch in beautiful Camden with its shaded streets and flower gardens. Arrive in Bar Harbor at the entrance to Arcadia National Park on Mount Desert island. Among Acadia's activities and attractions is a 20 mile scenic drive along the Park Loop Road. A series of carriage paths and foot trails allows hiking, climbing, biking, and horseback riding throughout the park. Bar Harbor itself is a bustling town filled with shops and restaurants. The annual Bar Harbor Festival in July and August is a platform for up and coming young artists. Bar Harbor also offers excellent whale watching opportunities.
Stay 2 nights

Day Six & Seven - Jackson (218 miles)

Begin early - you have a long drive ahead through rural Maine countryside to the White Mountains. This area claims all of New Hampshire's 48 peaks in excess of 4,000 ft and the highest mountain in the northeast - Mount Washington. Here you can take the Mt. Washington Auto Road to the summit and enjoy some of the finest views in New England. At the end of the eight mile route is the Observatory and the State Park building. The White Mountain National Forest encompasses 1,200 miles of hiking trails in 780,000 acres of forest and offers outstanding scenery and outdoor recreation opportunities.
Stay 2 nights.

Stop en route to Jackson in the resort town of North Conway - a shoppers paradise with a plethora of name brand factory outlets. North Conway village, located at the north end of the shopping strip is a colourful neighbourhood of brightly painted older storefronts on broad sidewalks, with a village green and plenty of parking. If you are travelling on to Lincoln, journey along the Kancamagus Highway. in the White Mountains, enjoy wonderful scenery, visit Franconia Notch and the 'Old Man of the Mountains', visit Heritage New Hampshire or Storyland or head to the Lakes region and experience the pleasures that the lakes have to offer - rent a boat or take a luncheon cruise.

Day Eight & Nine - Killington (155 miles)

If you spent the night in Jackson or North Conway, head along the Kancamagus Highway to Lincoln. This is New England's wildest scenic highway with no motorist services or homes on this road but holds considerable fascination for visitors. Continue to Hanover, the home of Dartmouth College before crossing into Vermont on your way to the Green Mountains. Stop at Quechee Gorge, Vermont's Mini Grand Canyon, for some breathtaking vistas of this 165 foot deep gorge. Plan to stop in the village of Woodstock with its traditional shops and covered bridge - an archetypal Vermont resort town. Enjoy Vermont's scenery enroute to Stowe to visit the Ben & Jerry's ice cream factory!
Stay 2 nights.

Day Ten - Stockbridge (162 miles)

Travel to Rutland, once centre to the Vermont marble industry, and be sure to stop in quaint Manchester Village on your way to the Berkshire Hills of Massachusetts. Visit Williamstown, a beautiful New England college town with tree-lines streets, classic architecture with an emphasis on white clapboard and black trim. The combination of old money and an academic environment has made Williamstown remarkable in its cultural resources. The Williamstown Theatre Festival takes place at the Williams College between late June and the end of August.
Continue to Lenox, where the Boston Symphony summers at Tanglewood. During the 1880's Lenox was the site of much frenetic building as many of the famous families with homes here - the Vanderbilts, Harrimans and Biddles - battled to out do one another by building ever more magnificent 'cottages', By the turn of the century the hills around Lenox and Stockbridge were dotted with some 75 villas and mansions with manicured lawns and formal gardens. Some still remain open to the public today. On to Stockbridge, the most popular town in the Berkshires and once home to Norman Rockwell, one of America's greatest artists. Stockbridge has a small town feel and epitomizes the image of a New England town. As in Lenox, there are some historic homes open to the public here and there is also the Norman Rockwell Museum, who was one of the towns most famous residents, which houses many of his original works.
Stay 1 night.

Days Eleven & Twelve - Newport (156 miles)

A busy day touring with several choices: visit Old Sturbridge Village, the largest living-history village in the Northeast.Old Sturbridge is a model of a rural New England town in the 1830', with more than 40 buildings and working homes from a water powered sawmill to a general store filled with goods. If you have time head for Mystic in Connecticut and the Mystic Seaport Museum, America's largest maritime museum, then continue to Newport on the southernmost tip of Aquidneck Island. Newport is the sailing capital of the world as well as one of the nation's most elegant summer resorts.
The area south of Newport is ringed by a famous 10-mile long route known as Ocean Drive, along which are perched some of New England's grandest mansions, known to their wealthy owners as 'cottages'. Some of the mansions are open to the public and include The Breakers built for Cornelius Vanderbilt and Marble House built for Alva Vanderbilt. Spend some time on one of Newport's spectacular beaches, or stroll the 3 mile Cliff Walk for more views of the mansions and the sea.
Enjoy Newport's restored waterfront and visit the many shops and the wide selection of restaurants.
Stay 2 nights.

Days Thirteen & Fourteen - Hyannis (75 miles)

Today, travel to Hyannis Cape Cod, famous as a summer resort with its white sandy beaches, picturesque harbours, art galleries, varied shopping, plentiful restaurants and abundance of attractions. Spend time in one of the many towns. Hyannis gained fame as the location of the summer house of President John F. Kennedy. The home is not open to the public and is not visible from the road but the John F. Kennedy Hyannis Museum located in the Old Town Hall displays many photographs of the family in Hyannis.
Take a visit to the historical village of Chatham or the colourful, artistic community of Provincetown. From Hyannis you could take the ferry to Nantucket for the day or from Woods Hole you could get the ferry to Martha's Vineyard only five miles off the coast.
Visit Sandwich, the Cape's oldest town and a small community with a town green and a village centre. It is home to the Hoxie House, built circa 1637 and therefore the oldest house on the Cape. The Heritage Plantation encompasses 76 acres of rhododendrons and more than 1,000 varieties of trees, shrubs and flowers.
Alternatively you could just spend the day lounging on one of the many beaches located on Cape Cod's 300 mile coastline.
Stay 2 nights.

Day Fifteen - Boston/Home (71 miles)

Plan to get the most from your day before heading for Boston's Logan Airport. Head north off the Cape on the Route 3 for Plymouth, where the Pilgrims landed in 1620 and spend some time exploring Plimoth Plantation, a living museum depicting a day in the life of the Pilgrims in 1627. Adjacent to the Plymouth rock is a replica of the same type of vessel as the Mayflower - which is surprisingly small. This is also your last chance to buy souvenirs as you now have to head back to Boston on the Route 3 and 93 to Logan Airport to drop your car off and catch your flight home.

Total Mileage - 1122 miles

Our Package Includes:

  •  Direct Return Flights
  •  14 nights accommodation and room tax 
  •  Car Hire 
  •  A comprehensive portfolio with a detailed day by day itinerary, driving instructions, maps and other information

For your convenience flights and car hire are included in our tour prices. If you already have a flight and just instead require hotel accommodation and car hire please contact us for a price.

Travelling in 2010? Please call us on (01892) 779900 or email info@awwt.co.uk for a competitive quotation.