Inn-Side New England

  • Maine + 2 more
  • Self Drive Ideas
  • 13 Days
from  £1,355pp
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Discover the beautiful scenery of New England staying in iconic Inns and hotels

A Free Personalised Road Book is included as standard with our Self Drive itineraries.


Please note: – This is a suggested itinerary only and is intended to give an overview of what is possible. All of our holiday itineraries are fully customisable and can be tailor-made to suit your own individual requirements.  If you would like to start in a different destination, use specific hotel accommodation, include an extra night here, a side-trip there and/or include tickets to an event please let your Discover North America travel specialist know. They’ll also book you the best value flights to ensure a seamless holiday experience.


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Day 1 Boston

Arrive Boston. Transfer to your hotel in downtown Boston for the overnight. This evening, explore Boston’s many restaurants, enjoy a show in Boston’s theatre district or stroll through lively Quincy Marketplace.

Day 2 Boston – Ogunquit – Scarborough (114mi/183km)

Pick up your rental car and depart for the Maine coast. Stop in Ogunquit. This quaint fishing hamlet is one of the most picturesque and enjoyed seaside resort villages in New England. Walk the mile-long Marginal Way over rocky ocean cliffs to Perkins Cove. Enjoy a mouth-watering lobster luncheon before continuing along the scenic coastal route through Kennebunkport dubbed “a magical place by the sea” into Scarborough. Located on a little peninsula and surrounded by water on three sides, this hotel boasts a stone fireplace and relaxed New England feel. Enjoy the Black Point Inn for the next 2 nights.

Day 3 Scarborough – Portland – Scarborough (15mi/24km)

This morning, take a short drive to Cape Elizabeth and visit the Portland Head Light & Museum, located along the spectacular shores of Fort Williams Park. The museum is located in the Keeper’s quarters. Then, head to Portland, an old seacoast town. Tour downtown’s Old Port historic district and some of the city’s historic homes. Portland is also a funky city filled with galleries, one-of-kind boutiques and shops, and incredible restaurants serving everything from New England clam chowder, lobster rolls and Maine seafood to nouveau cuisine.

Day 4 Scarborough – Jackson (69mi/111km)

Travel along scenic Sebago Lake to the NH White Mountains

Day 5 Jackson – White Mountains – Jackson (68mi/110km)

Today, travel through Franconia Notch, which offers magnificent views and unique sites. Visit The Flume Gorge resplendent with the offerings of each season or take the aerial tram to the summit of Cannon Mountain. Continue further and board the Cog Railway to the summit of Mt. Washington. A ride up Mount Washington on the world’s first mountain-climbing cog railway remains, as it has for well over a century, an exciting and unforgettable experience.

Day 6 Jackson

Enjoy the many opportunities of hiking and outdoor activities. Go outlet and tax-free shopping in nearby North Conway.

Day 7 Jackson – Shrewsbury (117mi/285km)

Scenic routes and covered bridges take you into Vermont. See Quechee Gorge, Vermont’s “Little Grand Canyon” before winding into Woodstock. A national magazine named Woodstock “The Prettiest Small Town in America” A lot of effort (and Rockefeller money) has gone into making sure the village keeps its pristine historic image. For instance, no utility wires appear overhead on downtown streets and the road you take to enter Woodstock will either cross a covered bridge, pass a picturesque horse farm or country store, or wind along the Ottauquechee River. After enjoying lunch at one of its fine restaurants, head west across winding country roads, into Shrewsbury to enjoy 2 nights at the Crisanver House.

Day 8 Shrewsbury – Shelburne – Stowe – Shrewsbury (223mi/359km)

Travel north along Vermont roads to visit the Shelburne Museum, one of the nation’s finest, most diverse, and unconventional museums of art and Americana. Over 150,000 works are exhibited in a remarkable setting of 39 exhibition buildings, 25 of which are historic and were relocated to the Museum grounds. Then, spend time in the charming village of Stowe, at the base of Mt. Mansfield. In Waterbury, visit Ben & Jerry’s Ice Cream Factory for a tour and tasting before returning to Shrewsbury.

Day 9 Shrewsbury – Williamstown – Lenox – Stockbridge (104mi/166km)

Depart Shrewsbury and travel along Vermont’s scenic Route 7 toward Williamstown, MA, a quintessential New England village known for the beauty of its surrounding mountains, for Williams College, and for the cultural attractions of its Theatre Festival and the Sterling and Francine Clark Art Institute. Choose to visit this museum and you will find an extraordinary collection of French Impressionist paintings, which take their place within a wider ensemble of masterworks that date from the Renaissance to the late 19th century and include an extensive collection of British and American silver. Continue into Stockbridge for the next 2 nights at the Red Lion Inn. This traditional inn, opened as a tavern in 1773, was rebuilt in 1897 after a fire destroyed the original structure. The Red Lion’s quintessential New England charm was immortalised by Norman Rockwell in his painting Stockbridge Main Street at Christmas.

Day 10 Stockbridge

Stroll this charming Dickensian-style village and visit the Norman Rockwell Museum, housing the world’s largest and most significant collection of original Rockwell art. Highlights include enduring favourites from Rockwell’s Saturday Evening Post covers. Head back to Sturbridge and visit Old Sturbridge Village to relive 1830’s rural New England life at this living history museum.

Day 11 Stockbridge – Newport – Sandwich (295mi/475km)

Depart Stockbridge for the coast of Rhode Island. Tour Newport’s Ocean Drive and Millionaire’s Row to see the magnificent mansions of the Gilded Age. Visit the Breakers, the largest of the Vanderbilt Family homes in Newport. Tour through the International Tennis Hall of Fame and enjoy lunch along the waterfront or at the historic Brick Marketplace. Before continuing to Cape Cod for the next two nights.

Day 12 Cape Cod

Today drive along the Cape Cod National Seashore to explore lighthouses, quaint coastal communities, and natural scenic beauty. Visit the lively artist colony of Provincetown, take a whale watch, or just lay on one of the Cape’s many sandy beaches. Don’t leave New England without feasting on Lobster, steamers, corn-on-the- cob and all the trimmings!

Day 13 Sandwich – Plymouth – Boston (60mi/97km)

Depart Sandwich and head east to Plymouth, Massachusetts, “America’s hometown”. See Plymouth Rock, upon which the Pilgrims first stepped. Board a replica of the Mayflower, the ship which carried the Pilgrims to the New World and visit Plimoth Plantation, a recreated village of 1627, where “interpreters” bring history to life. After a leisurely lunch along the water, travel into Boston for your departure flight.