29 days in New England Itinerary

29 days in New England Itinerary

Created using Inspirock New England trip itinerary maker

Plan created by another user.Make it yours

Route & dates

1
Bar Harbor, Mount Desert Island
— 4 nights
2
North Conway
— 3 nights
3
Ogunquit
— 4 nights
4
Boston
— 5 nights
5
Provincetown
— 4 nights
6
Sandwich
— 3 nights
7
Newport
— 5 nights

4
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Explore the numerous day-trip ideas around Bar Harbor: Winter Harbor (Whopaints Gallery & Schoodic Point). There's much more to do: take in the awesome beauty at Cadillac Mountain, hike along Gorham Mountain Trail, look for all kinds of wild species at Shore Path, and stroll through Carriage Roads.

To find ratings, traveler tips, photos, and other tourist information, use the Bar Harbor tour itinerary maker website.

Miami to Bar Harbor is an approximately 9.5-hour flight. You can also drive; or take a bus. In October, Bar Harbor is much colder than Miami - with highs of °F and lows of °F. Wrap up your sightseeing on the 6th (Tue) to allow time to drive to North Conway.

Things to do in Bar Harbor

Parks Outdoors Trails

Side Trips

Acadia National Park, Winter Harbor
Highlights from your plan
Schoodic Point ©
Schoodic Point
Cadillac Mountain ©
Cadillac Mountain
Boat Tours & Water Sports

3
nights
North Conway

North Conway ©
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.
Explore the numerous day-trip ideas around North Conway: Mount Washington Auto Road (in Gorham), Dog Mountain Home of Stephen Huneck Gallery (in Saint Johnsbury) and Franconia (Franconia Notch State Park & Flume Gorge). And it doesn't end there: cruise along Kancamagus Highway, take in the awesome beauty at Rocky Gorge, look and learn at Mount Washington Observatory Weather Discovery Center, and delve into the lush surroundings at White Mountain National Forest.

To find maps, photos, where to stay, and tourist information, go to the North Conway road trip planner.

You can drive from Bar Harbor to North Conway in 4.5 hours. Alternatively, you can do a combination of flight and bus; or do a combination of bus and car. In October in North Conway, expect temperatures between °F during the day and °F at night. Finish up your sightseeing early on the 9th (Fri) so you can go by car to Ogunquit.

Things to do in North Conway

Parks Outdoors Scenic Drive

Side Trips

Franconia, Mount Washington Auto Road, Dog Mountain Home of Stephen Huneck Gallery, White Mountain National Forest, Rocky Gorge
Highlights from your plan
Kancamagus Highway ©
Kancamagus Highway
White Mountain National Forest ©
White Mountain National Forest
Franconia Notch State Park ©
Franconia Notch State Park

4
nights
Ogunquit

Ogunquit ©
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.
Get out of town with these interesting Ogunquit side-trips: Portland (Victoria Mansion, The Cathedral Of The Immaculate Conception, &more), Portland Head Light (in Cape Elizabeth) and The Wilson Memorial Chapel (in East Boothbay). There's much more to do: appreciate the extensive heritage of Marginal Way Walkway, take in nature's colorful creations at Coastal Maine Botanical Gardens, enjoy the sea views from Nubble Lighthouse, and kick back and relax at Ogunquit Beach.

To find maps, other places to visit, traveler tips, and tourist information, go to the Ogunquit day trip planning app.

You can drive from North Conway to Ogunquit in 2 hours. Alternatively, you can take a bus. Expect little chillier evenings in Ogunquit when traveling from North Conway in October, with lows around °F. Cap off your sightseeing on the 13th (Tue) early enough to go by car to Boston.

Things to do in Ogunquit

Historic Sites Parks Beaches

Side Trips

Portland, Coastal Maine Botanical Gardens, Pemaquid Point Lighthouse, Nubble Lighthouse, Portland Head Light
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Portland Head Light ©
Portland Head Light
Coastal Maine Botanical Gardens ©
Coastal Maine Botanical Gardens

5
nights
Boston

Boston ©
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.
Venture out of the city with trips to Dolphin & Whale Watching (in Gloucester) and Salem (Peabody Essex Museum, The House of the Seven Gables, &more). And it doesn't end there: explore the world behind art at Museum of Fine Arts, buy something for everyone on your list at Faneuil Hall Marketplace, take a stroll through North End, and get to know the fascinating history of Freedom Trail.

To find traveler tips, where to stay, photos, and more tourist information, use the Boston trip website.

Traveling by car from Ogunquit to Boston takes 1.5 hours. Alternatively, you can do a combination of taxi and train; or take a bus. Traveling from Ogunquit in October, you can expect nighttime temperatures to be a bit warmer in Boston, with lows of °F. Finish your sightseeing early on the 18th (Sun) to allow enough time to ride a ferry to Provincetown.

Things to do in Boston

Museums Parks Historic Sites

Side Trips

Salem, Dolphin & Whale Watching
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden
Freedom Trail ©
Freedom Trail

4
nights
Provincetown

Provincetown ©
A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
Get out of town with these interesting Provincetown side-trips: Monomoy National Wildlife Refuge (in Chatham), Eastham (Coast Guard Beach & Salt Pond Visitor Center) and Nauset Beach (in Orleans). There's still lots to do: enjoy the sand and surf at Cape Cod National Seashore, stroll through Herring Cove Beach, get lost in a book at Provincetown Library, and take a leisurely stroll along MacMillan Wharf.

For ratings, more things to do, where to stay, and more tourist information, go to the Provincetown trip itinerary site.

Ride a ferry from Boston to Provincetown in 2.5 hours. Alternatively, you can do a combination of ; or drive. In October in Provincetown, expect temperatures between °F during the day and °F at night. Wrap up your sightseeing on the 22nd (Thu) to allow time to drive to Sandwich.

Things to do in Provincetown

Parks Beaches Outdoors

Side Trips

Eastham, Monomoy National Wildlife Refuge, Cape Cod National Seashore, Nauset Beach
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Pilgrim Monument & Provincetown Museum ©
Pilgrim Monument & Provincetown Museum
Race Point Beach ©
Race Point Beach

3
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. You'll find plenty of places to visit near Sandwich: Farm Neck Golf Club (in Oak Bluffs), Highfield Hall & Gardens (in Falmouth) and Stone Bridge Farm (in Acushnet). There's still lots to do: get curious at Sandwich Glass Museum, appreciate the history behind Plymouth Rock, get engrossed in the history at Plimoth Plantation, and grab your bike and head to Shining Sea Bikeway.

To see photos, where to stay, reviews, and more tourist information, you can read our Sandwich trip itinerary maker.

Drive from Provincetown to Sandwich in 1.5 hours. Alternatively, you can take a bus. In October, plan for daily highs up to °F, and evening lows to °F. Finish your sightseeing early on the 25th (Sun) to allow enough time to drive to Newport.

Things to do in Sandwich

Museums Outdoors Parks

Side Trips

Falmouth, Plymouth, Farm Neck Golf Club, Cape Cod Canal, Stone Bridge Farm
Highlights from your plan
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Sandwich Glass Museum ©
Sandwich Glass Museum
Old King's Hwy ©
Old King's Hwy

5
nights
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Venture out of the city with trips to Mystic (Mystic Seaport Museum & Mystic River Bascule Bridge), Chatham Lighthouse Beach (in Chatham) and Chatham Marconi Maritime Center (in North Chatham). The adventure continues: examine the collection at The Breakers, admire all the interesting features of Ocean Drive Historic District, experience rural life at Young Family Farm, and get to know the fascinating history of Cliff Walk.

To find ratings, where to stay, maps, and other tourist information, go to the Newport online trip planner.

Getting from Sandwich to Newport by car takes about 1.5 hours. Other options: take a bus; or do a combination of bus and train. October in Newport sees daily highs of °F and lows of °F at night. Finish your sightseeing early on the 30th (Fri) to allow enough time to travel back home.

Things to do in Newport

Historic Sites Outdoors Parks

Side Trips

Mystic, Chatham, Beavertail Lighthouse and Park, Young Family Farm
Highlights from your plan
The Breakers ©
The Breakers
Cliff Walk ©
Cliff Walk
Mystic Seaport Museum ©
Mystic Seaport Museum

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