Inn-side New England | Fly Drive Holiday

Days 1-2

Boston

On arrival in Boston, make your way to the renowned Fairmont Copley Plaza in the centre of the city. You will have time to explore stately Beacon Hill with its elegant Georgian-style houses, follow the 2.5 mile Freedom Trail meandering through the city passing 16 of the USA’s most iconic buildings and historic sites. Visit the Faneuil Hall and Quincy Marketplaces. Museums abound ranging from the Boston Tea Party ships and museum to the Harvard Museum of National History and much in between.

2 nights Boston – Fairmont Copley Plaza Hotel

Days 3-4

Boston to Scarborough

Collect your rental car and leave Boston heading 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, where a stop for a cup of tea is highly recommended, into Scarborough and out to Prouts Neck where you will find the Black Point Inn. The Inn is surround by water on three sides, has a renowned ocean-front restaurant, the Chart Room and 25 delightfully decorated rooms. (Dinner reservations recommended).

While in Scarborough, we would recommend you drive out to Cape Elizabeth to visit the Portland Head Light and Museum and then head into Portland. Walk around the Old Port’s historic district and some of the many galleries and boutiques.

2 nights Scarborough – Black Point Inn

Days 5-7

Scarborough to Jackson

A leisurely drive today past the Sebago Lake to the pretty town of Jackson in New Hampshire’s White Mountains, where you will spend three nights at the Inn at Thorn Hill and Spa.

There is so much to do in the White Mountains, whether you love the great outdoors or some retail therapy. There are many hikes, one for every ability. You can head up into the treetops on the Bretton Woods Canopy Tour or whitewater raft through the forest. For the more sedentary, there is outlet and tax-free shopping in nearby North Conway plus plenty of boutiques and art galleries to explore.

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 Mount 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. (tickets are included in the price)

3 nights Jackson – Inn at Thorn Hill and Spa

Days 8-9

Jackson to Newfane

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 Newfane to enjoy 2 nights at the Four Columns Inn. (other guests have included Mick Jagger, Paul Newman and Henry Kissinger to name but a few)  If you are travelling as a family, you might like to stay at Naulakha, Rudyard Kipling’s former home and where the Jungle Book was written. (A 3-night minimum stay is required) or one of the smaller surrounding properties.

Traverse the winding 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 and while you are there a visit Ben & Jerry’s Ice Cream Factory is a must for all ice-cream lovers.

2 nights Newfane – Four Columns Inn

Days 10-11

Newfane to Stockbridge

Today your drive takes you along Vermont’s scenic Route 7 toward Williamstown, MA, a quintessential New England village known for the beauty of its surrounding mountains. Also Williams College, the Theatre Festival and the Sterling and Francine Clark Art Institute which houses an extraordinary collection of French Impressionist paintings, amongst a wider collection masterpieces ranging from the Renaissance to the late 19th century as well as 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 Lions quintessential New England charm was immortalized by Norman Rockwell in his painting Stockbridge Main Street at Christmas .

Spend the next day exploring the Dickensian-style village of Stockbridge: be sure to visit.

Norman Rockwell Museum, housing the worlds largest and most significant collection of original Rockwell art and the Old Sturbridge Village to relive 1830’s rural New England life at this living history museum.

2 nights Stockbridge – Red Lion Inn

Days 12-13

Stockbridge to Sandwich

Depart Stockbridge for the coast of Rhode Island. Tour Newport’s Ocean Drive and Millionaires 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 at the Belfry Inn in Sandwich.

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 Capes many sandy beaches. Don’t leave New England without feasting on lobster, steamers, corn-on-the- cob and all the trimmings! If you would like an extra day or two on Cape Cod, just let us know.

2 nights Sandwich – Belfry Inn

Day 14

Sandwich to Boston

Today is your last day and you need to head back to Boston Airport, but on the way, do stop at 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 Plymouth Plantation, a recreated village of 1627, where interpreters bring history to life.