29 days in New England Itinerary

29 days in New England Itinerary

Created using Inspirock New England route planner

Make it your trip
Fly
1
Hyannis
— 3 nights
Drive
2
Newport
— 4 nights
Drive
3
Lenox
— 4 nights
Drive
4
North Conway
— 4 nights
Drive
5
Bar Harbor, Mount Desert Island
— 5 nights
Drive
6
Ogunquit
— 2 nights
Drive
7
Boston
— 6 nights
Fly

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Hyannis

— 3 nights

Capital of Cape Cod

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Your cultural itinerary includes sights like Sandwich Glass Museum and Plimoth Patuxet. Get in touch with nature at Hyannis Whale Watcher Cruises and Monomoy National Wildlife Refuge. Explore the numerous day-trip ideas around Hyannis: Nobska Point Lighthouse (in Woods Hole) and Plymouth (Mayflower II & Plymouth Rock). And it doesn't end there: kick back and relax at Cape Cod National Seashore, contemplate the long history of Edward Gorey House, and see the interesting displays at John F Kennedy Hyannis Museum.

To see reviews, photos, ratings, and more tourist information, go to the Hyannis trip planning site.

Amsterdam, The Netherlands to Hyannis is an approximately 11.5-hour flight. Traveling from Amsterdam to Hyannis, you'll gain 6 hours due to the time zone difference. October in Hyannis sees daily highs of 20°C and lows of 10°C at night. Wrap up your sightseeing on the 6th (Wed) to allow time to drive to Newport.

Things to do in Hyannis

Outdoors · Parks · Museums · Wildlife

Side Trips

Newport

— 4 nights

City by the Sea

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Do some cultural sightseeing at The Breakers and Ocean Drive Historic District. Take a break from the city and head to Cliff Walk and East Over Reservation. Explore the numerous day-trip ideas around Newport: Lizzie Borden House (in Fall River) and Mystic Seaport Museum (in Mystic). There's lots more to do: admire the striking features of The Elms, steep yourself in history at Fort Adams State Park, examine the collection at Newport Car Museum, and take in the architecture and atmosphere at St. Mary's Catholic Church.

To find where to stay, other places to visit, traveler tips, and other tourist information, go to the Newport trip itinerary maker tool.

Getting from Hyannis to Newport by car takes about 2 hours. Other options: take a bus. Expect a daytime high around 20°C in October, and nighttime lows around 11°C. Cap off your sightseeing on the 10th (Sun) early enough to go by car to Lenox.

Things to do in Newport

Historic Sites · Museums · Outdoors · Parks

Side Trips

Lenox

— 4 nights
Lenox is an affluent town in Berkshire County, Massachusetts, United States. Satisfy your inner culture vulture at Norman Rockwell Museum and Hildene, The Lincoln Family Home. Step out of the city life by going to Pleasant Valley Sanctuary and Mount Greylock State Reservation. Venture out of the city with trips to MASS MoCA (in North Adams), Old Drake Hill Flower Bridge (in Simsbury) and The Clark Art Institute (in Williamstown). Next up on the itinerary: stroll through Ashuwillticook Rail Trail, take in the awesome beauty at Monument Mountain, cruise along Concepts of Art Lenox Judaica, and contemplate in the serene atmosphere at National Shrine of the Divine Mercy.

For ratings, photos, and other tourist information, read our Lenox road trip planning app.

Traveling by car from Newport to Lenox takes 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. Plan for slightly colder nights when traveling from Newport in October since evenings lows in Lenox dip to 5°C. Finish your sightseeing early on the 14th (Thu) so you can drive to North Conway.

Things to do in Lenox

Museums · Parks · Historic Sites · Nature

Side Trips

North Conway

— 4 nights
North Conway combines colonial New England architecture with outlet shops selling goods from some of the world's most recognizable brands, all set amid the scenery of the White Mountains.
Satisfy your inner culture vulture at Flume Gorge and Saco River Covered Bridge. Get outdoors at Kancamagus Highway and Bretton Woods Canopy Tour. You'll find plenty of places to visit near North Conway: West Rattlesnake Mountain (in Holderness), Cascade Falls (in Woodstock) and Franconia Notch State Park (in Franconia). Next up on the itinerary: explore the striking landscape of White Mountain National Forest, look and learn at Mount Washington Observatory Weather Discovery Center, take in the dramatic scenery at Rocky Gorge, and pause for some serene contemplation at The Little White Church.

To see more things to do, where to stay, reviews, and more tourist information, refer to the North Conway trip planner.

Traveling by car from Lenox to North Conway takes 5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In October, plan for daily highs up to 19°C, and evening lows to 8°C. Wrap up your sightseeing on the 18th (Mon) early enough to drive to Bar Harbor.

Things to do in North Conway

Nature · Parks · Outdoors · Scenic Drive

Side Trips

Bar Harbor, Mount Desert Island

— 5 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Get a sense of the local culture at The Seal Cove Auto Museum and St. Saviour's Church :. Step out of the city life by going to Cadillac Mountain and Shore Path. Venture out of the city with trips to Schoodic Point (in Winter Harbor), Camden (Mount Battie & Curtis Island Light) and Fernald's Neck Preserve (in Lincolnville). Next up on the itinerary: get a new perspective on things with Boat Tours & Water Sports, cruise along Park Loop Road, trek along Gorham Mountain Trail, and grab your bike and head to Carriage Roads.

For ratings, maps, where to stay, and other tourist information, go to the Bar Harbor online journey planner.

You can drive from North Conway to Bar Harbor in 4.5 hours. Alternatively, you can do a combination of car and bus; or do a combination of bus and flight. In October, daytime highs in Bar Harbor are 17°C, while nighttime lows are 6°C. Finish your sightseeing early on the 23rd (Sat) to allow enough time to drive to Ogunquit.

Things to do in Bar Harbor

Parks · Outdoors · Trails · Nature

Side Trips

Ogunquit

— 2 nights
Ogunquit means "beautiful place by the sea" in the language of the Native Americans who inhabited the region long ago, and this remains an accurate description of this holiday destination today.
Start off your visit on the 24th (Sun): enjoy the sea views from Nubble Lighthouse, take in the exciting artwork at PANACHE FINE JEWELRY AND ART GALLERY, then appreciate the extensive heritage of Marginal Way Walkway, and finally take in the dramatic natural features at Perkins Cove. Get ready for a full day of sightseeing on the 25th (Mon): look for all kinds of wild species at Wells Reserve at Laudholm, look for all kinds of wild species at Rachel Carson National Wildlife Refuge, and then enjoy the sand and surf at Ogunquit Beach.

To see maps, more things to do, and tourist information, read Ogunquit trip itinerary app.

You can drive from Bar Harbor to Ogunquit in 4 hours. Alternatively, you can do a combination of flight and bus; or do a combination of bus, train, and taxi. October in Ogunquit sees daily highs of 19°C and lows of 3°C at night. Finish your sightseeing early on the 25th (Mon) so you can drive to Boston.

Things to do in Ogunquit

Parks · Wildlife · Historic Sites · Beaches

Side Trips

Boston

— 6 nights

Beantown

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Freedom Trail and The House of the Seven Gables are good opportunities to explore the local culture. Visit Louisa May Alcott's Orchard House and Trinity Church for their historical value. Explore the numerous day-trip ideas around Boston: Dolphin & Whale Watching (in Gloucester) and Salem (Peabody Essex Museum, Salem Witch Museum, &more). Next up on the itinerary: admire the masterpieces at Museum of Fine Arts, get engrossed in the history at USS Constitution Museum, walk around Boston Common, and explore the galleries of Isabella Stewart Gardner Museum.

To see reviews, other places to visit, ratings, and more tourist information, read our Boston planner.

You can drive from Ogunquit to Boston in 1.5 hours. Other options are to do a combination of taxi and train; or take a bus. Traveling from Ogunquit in October, expect a bit warmer with lows of 11°C in Boston. Cap off your sightseeing on the 31st (Sun) early enough to travel back home.

Things to do in Boston

Museums · Historic Sites · Parks · Tours

Side Trips