Explore New England starting from Boston

• from / to Boston
• 14 days / 1,750 km
• Best time to travel: May to October

Boston was founded by Puritans in 1630, ten years after the first immigrants landed near the Plymouth Rock. At that time, Boston became one of the most important port cities and was the largest British settlement in Ameriapprox. The Old South Meeting House is one of the many historic sites that can be found in the city. It was the frequent scene of demonstrations and protest marches in the 18th century. The protest that took place in December 1773 was historically the most important one. It became the catalyst for the “Boston Tea Party” and the subsequent War of Independence. You can also visit the Bunker Hill Monument, which commemorates the battle fought here in June 1775.

The recommended station is Faneuil Hall, which is a marketplace including Quincy Market, North Market, and South Market. The old and previously dilapidated market halls and warehouses were restored to create the most popular “playground” in the city. The shops, market stalls, restaurants, and street cafés invite tourists to take a short break. Beacon Hill is located directly above the Boston Common, which is a public park, and is one of the beautiful residential areas. The Boston Tea Party Ships and Museum is located on the Congress Street Bridge on the Harborwalk. The ship that carries the name “Beaver II” is a replica of the original one.

Cambridge, with the very famous Harvard University, is located across the Charles River from Boston. The university, which is the oldest one in the country, was founded in 1636. The buildings around the historic “yard” on Harvard Square present a cross-section of American architecture.

Highlights & Tips

Walking around Boston
The Freedom Trail leads you past many historic and architecturally interesting buildings. The trail is marked by a red line on the sidewalk and begins at Boston Common Visitor Information Center. For a small price, you can buy a map of Boston where you will be able to familiarize yourself with the facts on the history of Boston and its most impressive buildings.

Boston – Portland

Suggested route: Boston – Portsmouth – Kennebunk – Portland

Stage distance: approx. 108 miles / 180 km

You will pass many old villages on the road from Boston to Portland. Over the years, they became popular holiday resorts, such as Kennebunkport, where you can also see the summer residence of the former President Bush and his family.

Salem is famous due to the persecution of witches and their trials. You can track the timeline of these events in the Salem Witch Museum. In Portsmouth, you will go back in time. The houses in this area come from the early colonial period, between the 17th and the 19th centuries. Portsmouth was once named Strawberry Banke and was the home port for merchant shipping, which contributed to the residents’ affluence. You will also walk through the narrow streets of the picturesque Old Town District.

Portland, the destination for today, is the largest city in Maine and has an outstanding location in the near vicinity of Casco Bay. The waterfront of the Old Port Exchange, which was the place of transhipment of such goods as oil, timber, and fish in the last century, is one of the interesting locations in the city. Warehouses and many Victorian homes, almost all of which were damaged in the Great Fire of 1866, were restored in the 1970s and transformed into restaurants and shops.

On Congress Street, which is the main street of the city, you can find theatres, museums, and a philharmonic hall. The Portland Museum Of Art is one of the highlights of the city. On Munjoy Hill, you will have an excellent view of Portland, which extends between Casco Bay, Back Cove, and the Fore River. Additionally, Cape Elizabeth and the Portland Head Light, Maine’s most photographed lighthouse, are worth visiting.

Highlights & Tips

Beautiful views of Portland
Munjoy Hill will be a great vantage point to admire the whole City of Portland, which extends between Casco Bay, Back Cove, and the Fore River.

Portland – Bar Harbour

Suggested route: Portland – Bath – Rockport – Camden – Bar Harbour

Stage distance: approx. 162 miles / 260 km

Lobster will be the theme of today's route as it is depicted on various billboards and restaurant signs along the way. It is possible to see the symbol of the City of Bath already from afar – these are the giant cranes of the Bath Iron Works. The shipyard is one of the largest employers in Maine and has been providing ships for the U. S. Navy for more than a hundred years. The road to Wiscasset, which claims to be the “prettiest village in Maine,” runs along a line of mixed forest.

Rockland is a modern seaport. Its historic Main Street is very interesting architecturally. The large bustling port is not only a centre of lobster fishing but also a home to the largest Maine Windjammer Fleet. There is a possibility to participate in short cruises and long excursions. Another classic example of Maine’s idyllic places is the city of Rockport, as its houses are located in a semi-circle on the slope above the port. Camden also presents itself as a beautiful place between the majestic coastal mountains and Penobscot Bay. It is considered to be one of the most charming villages in New England.

Continue your trip to Bar Harbour, which in the past was the famous retreat of the aristocracy. Millionaires such as J. P. Morgan, Joseph Pulitzer, and John D. Rockefeller built their cottages in the village and peacefully enjoyed the harsh beauty of the surrounding landscape. In 1916, they bought more than 12,000 acres of land and donated it to the state as Acadia National Park. With a diameter of 25 km, the area is very small in comparison to the vast national parks of the Southwest. However, the beautiful coastline, hard-to-reach islands, large lakes, stunning mountain ranges, granite cliffs, and dense forests will be enough for a multi-day program.

Highlights & Tips

Postcard idyll of Maine from above
The most beautiful view of Rockport can be admired from the spot by the Children’s Chapel on Vesper Hill.

There is also a beautiful view of Camden, from the Camden Hills State Park. The toll road, which leads to the summit of Mount Battie, branches off north of Camden. You will be able to admire the picturesque and panoramic view of the idyllic harbour, the Camden Hills, and Penobscot Bay. The top can be reached on foot as well. The steep, mile-long Mount Battie South Trail begins on Megunticook Street, located north of the town square.

Cadillac Mountain is located near Bar Harbour and offers beautiful views of the rugged coastline with all the islands, rocks, and forests.

Bar Harbour – North Conway / White Mountains

Suggested route: Bar Harbour – Skowhegan – Bethel – Jackson – North Conway

Stage distance: approx. 240 miles / 400 km

The route continues from Bar Harbour along the idyllic Lake Wilson. Bethel can be found just before the border with New Hampshire and is an ideal location to take a rest or organise a picnic. The historic settlement was established in 1774 and is located in the near vicinity of the White Mountain National Forest. The area is a price-attractive holiday paradise for hikers, canoeists, anglers, and skiers every season. Eight miles south of Gorhem begins a route which leads to Mount Washington, which is the highest peak located east of the Rocky Mountains. It is 1,917 meters high.

North Conway is the commercial centre of the recreational area of Mount Washington Valley, which is famous for its beautiful canyons, gorges, lakes, and waterfalls. Cathedral Ledge is a recommended attraction. It is located northwest from North Conway at the end of the River Road on the Saco River. It is always possible to spot bold climbers trying their hand at impressing the awe-struck audience with their dramatic art. The wide panoramic view of the whole valley is free of charge.

Jackson is an elegant ski resort. In the past, it was visited by artists who wanted to capture the beauty of nature on canvas and take pictures of the covered bridge. Today, there are only 55 of such bridges in the whole area of New England.

The White Mountain National Forest is mostly covered with mixed forests. There is great likelihood that you might spot a moose as they tend to cross the street occasionally. You will come across Pinkham Notch which is a 619-meter mountain pass leading to Glen Ellis Falls. From the car park, you can take the downhill path to the falls. Then, you will be on the east side of the Presidential Mountain Range. The peaks along the range are named after the Presidents of the United States: Jackson, Eisenhower, Washington, Adams, and Madison.

The journey continues to the Crawford Notch State Park. There is a hiking trail which leads to Arethusa Falls, located approximately 1.5 miles (2.4 km) from the road near Crawford Notch. It is one of the highest waterfalls in New Hampshire, as it is 200 feet (61 meters) high.

Highlights & Tips

The Cog Railway
The Mount Washington Cog Railway has been operating on the western flank of the mountain at Bretton Wood since 1869. It is considered to be the second steepest rack railway in the world. At the beginning, it was the world’s first rack railway that was climbing uphill. Now, it is still a major tourist attraction.

Caution, bears!
It is often possible to encounter wild bears in the White Mountain National Forest. Please observe the instructions that can be found on the official website.

North Conway – Rutland

Stage distance: approx. 165 miles / 265 km

Suggested route: North Conway – St. Johnsbury – Woodstock – Rutland

Vermont is known worldwide for its marble and granite as well as for the Green Mountains, which serve as a recreation area both during the summer and winter. The charming town of Woodstock, which has nothing to do with the legendary music festival, is a very attractive stopover. In the centre of the city, tourists can admire a covered bridge, which spans the Ottauquechee River, and a number of beautifully renovated houses from the 19th century.

Proctor is located in the vicinity of Rutland and is famous for the Vermont Marble Museum.The area is rich in marble deposits. At the beginning of the 20th century, the Vermont Marble Company was one of the largest US companies. Rutland itself was founded in 1761 and named after the Duke of Rutland. In the 1840s, the business connected with the elegant stone started to flourish in the area. As a result, the world-famous Italian marble quarries in Carrara became unproductive.

Highlights & Tips

Historic information board
All of the major local events are handwritten on the large Town Crier Chalkboard which has been located in Woodstock for generations. What is more, you will be able to learn here about all of the most popular city tours.

Rutland – Sturbridge

Suggested route: Rutland – Manchester – Bennington – Williamstown – Stockbridge – Sturbridge

Stage distance: approx. 180 miles / 275 km

On the western edge of the Green Mountain National Forest, the route leads up and down through a peaceful landscape full of small picturesque villages. Manchester has been a popular summer destination since the 19th century and is renowned for its connection with Abraham Lincoln, who often spent the holiday at the foot of the Green Mountains with his family. The town is a great option for a stroll to discover attractive shops, typical covered bridges, and sidewalks made of finest marble.

Bennington is especially proud of its role in the American struggle for independence. Its patriotic importance is symbolized by the Bennington Battle Monument, which is 93 meters tall. It is the tallest structure in the whole Vermont area and can be seen from every spot in the town. The Old First Church with its three-tiered bell tower is one of the most beautiful churches in New England. It is also considered to be a landmark of the city.

Williamstown, with its park-like grounds, beautiful church, and well-maintained colonial buildings, is not only a visual jewel but also one of the elite college towns in the US.

"The Red Lion Inn" is a country inn with a large yard where you can find numerous rocking deck chairs. It is considered to be the central attraction and the focal point of the nightlife in Stockbridge.

The contemplative Sturbridge located in Worcester County has one of the most beautiful open-air museums in New England (and the largest so far). It can be found among the hills of central Massachusetts. Inside, you will learn about the everyday life in the rural New England of the 1830s.

Highlights & Tips

Art in the Green Mountains
You can visit the Sterling and Francine Clark Art Institute as well as the Williams College Museum of Art.The former offers works by Durer, Picasso, or Renoir, whereas the latter is famous for its interesting exhibits which range from antique vases from Ancient Greece to Andy Warhol’s pop art.

Sturbridge – Newport

Suggested route: Sturbridge – Norwich – Newport

Stage distance: approx. 124 miles / 200 km

Mystic is a town located along the way to Newport. Its biggest attraction is the Mystic Seaport Outdoor Museum that can be found in a historic port with ships. While travelling towards Newport, a lovely tourist resort from the 19th century, you can admire the charming villas with awnings as well as sailboats in the Rhode Island Sound. Newport was founded in the 17th century by the first Quakers as well as a group of Jewish families who fled from Massachusetts to seek refuge from religious intolerance. After the American Civil War, Newport became famous as a summer residence of wealthy families.

Visit the Old Colony House on Washington Square. It was constructed in 1739 and was part of the Royal Government. The Trinity Church was the first Anglican church in the United States. In Newport, there is also the oldest synagogue in the whole country. What is more, Chateau-sur-Mer, a Victorian-style manor house, is also worth paying a visit.

Highlights & Tips

Maritime Museum in Mystic
The Mystic Seaport was founded in 1929 to preserve the historical heritage of the seafaring town of Mystic. Today, the museum site covers almost eight hectares and offers a restored sea village with shops and docks, children’s museum, repair yard, planetarium, and a number of permanent and temporary exhibitions which include figureheads, scrimshaws, paintings, navigational instruments, and models.

Newport – Cape Cod

Suggested route: Newport – Fall River – New Badford – Cape Cod

Stage distance: approx. 75 miles / 120 km

One of the major attractions of Fall River is the Marine Museum where, among numerous other models, you can also see the Titanic. In the 19th century, New Bedford was one of the most important ports in the world when it came to whaling. The plot of Herman Melville's Moby Dick starts in this particular location. The town still thrives owing to the port. However, the excursion steamers have not replaced the fishing trawlers yet. In addition to thousands of Irish, Italian, Norwegian, and French-Canadian residents, 60% of more than 90,000 residents are Portuguese. What is more, a number of summer festivals are held in the area of the renovated Waterfront Historic District. The participants from the Azores and Cape Verde dressed in colourful clothes are always cheerfully dancing through the narrow streets.

Our destination of the day is the last natural highlight of the trip. Cape Cod, more than any other region of New England, is famous for its literature and poetry. What is more, a large part of the area is covered by the Cape Cod National Seashore, which is a nature reserve.

Wellfleet was once a major whaling port. Today, it is frequently visited by oyster lovers. Those who are interested in the unique natural environment will surely enjoy the ride along the Chequessett Neck Road or a long walk on the Great Island Trail in the direction of Jeremy’s Point.

In the near vicinity of Truro, you will have to search for long to find places even remotely resembling towns. These can be found in the solitude of quiet and fragrant pine forests. Provincetown stands in opposition to such settlements, as it is full of restaurants, pubs, galleries, and souvenir shops. It was also home to many artists, including playwrights like Eugene O'Neill, Tennessee Williams, and Sinclair Lewis. One of the major tourist attractions in the area is whale watching.

Hyannis lies in the Mid-Cape, 65 kilometres from Plymouth and 70 kilometres from Provincetown. From the mid-1920s the place was used by the Kennedys as a summer retreat. The relationship of the 35th President of the United States to Cape Cod is presented on large-format photos that can be admired in the John F. Kennedy Hyannis Museum.The town was the location for President Kennedy’s Summer White House.

Chatham’s promenade at night is one of the city’s highlights. It offers a large array of toy stores, antiques galleries, bookshops, and cafés. The summer big band concerts held in the Kate Gould Park on Fridays are a magnet for visitors.

Highlights & Tips

Choose a train ride or a ferry
The Cape Cod Scenic Railroad starts its tour in Hyannis and continues through the peninsula. Whereas, the ferries to Martha’s Vineyard are waiting for the visitors in the port.

Boat tour to Monomy Island
Anyone who loves boat riding should try Monomoy Island Excursions, which offer tours to Monomoy Island during which you can admire seal colonies. The island is home to more than 250 bird species. During the trip, you will be able to experience the magical ambiance of Cape Cod, which has fascinated generations of painters and photographers for centuries.

Hyannis (Cape Cod) – Boston

Suggested route: Hyannis (Cape Cod) – Plymouth – Boston

Stage distance: approx. 75 miles / 120 km

If you still have time for the last stage, you could visit the Plimoth Plantation and the Mayflower ship located in the port of Plymouth. In 1620, the Pilgrim Fathers with 101 other people came on board of the Mayflower and landed on the coast of the present-day Massachusetts. They founded the colony of Plymouth. Their first settlement was built near the coast. The Museum of Plimoth Plantation, which was established in 1947, is a speculative reconstruction of the area from 1627. The attraction has been reconstructed down to the finest detail with its meticulously prepared buildings, animals, and actors depicting scenes as in a real 17th-century English village. The actors employed at the museum speak with an English dialect which additionally helps to immerse in a place from over 350 years ago.

Furthermore, the Wampanoag Native American settlement is also part of the museum. Today’s Native Americans present the way of living of their ancestors and explain the production of boats from tree trunks and the construction of huts and houses from bark. The reconstructed Mayflower II, which also belongs to the museum, is located at Plymouth Rock - the traditional site of disembarkation of the Pilgrim Fathers.