31 days in New England Itinerary

31 days in New England Itinerary

Created using Inspirock New England trip planner

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

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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.
Change things up with these side-trips from North Conway: West Rattlesnake Mountain (in Holderness), Franconia Notch State Park (in Franconia) and Bretton Woods Canopy Tour (in Bretton Woods). Next up on the itinerary: cruise along Kancamagus Highway, admire the sheer force of Glen Ellis Falls, get great views at Cathedral Ledge, and stop by Zeb's General Store.

To see traveler tips, where to stay, ratings, and tourist information, read North Conway trip website.

Oklahoma City to North Conway is an approximately 7.5-hour flight. You can also drive; or take a bus. Traveling from Oklahoma City to North Conway, you'll lose 1 hour due to the time zone difference. Prepare for slightly colder weather when traveling from Oklahoma City in October: high temperatures in North Conway hover around 62°F and lows are around 45°F. Finish your sightseeing early on the 5th (Wed) so you can drive to Ogunquit.

Things to do in North Conway

Parks · Nature · Wildlife · Outdoors

Side Trips

Ogunquit

— 4 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.
Venture out of the city with trips to Portland Head Light (in Cape Elizabeth), L.L. Bean Factory Store (in Freeport) and Portland (Allagash Brewing Company & Beer Tastings & Tours). There's lots more to do: appreciate the extensive heritage of Marginal Way Walkway, explore the striking landscape at Perkins Cove, enjoy the sea views from Nubble Lighthouse, and take a tour by water with Boat Tours & Water Sports.

To see maps, reviews, and tourist information, use the Ogunquit itinerary planning app.

Traveling by car from North Conway to Ogunquit takes 2 hours. Alternatively, you can take a bus. Traveling from North Conway in October, plan for little chillier nights in Ogunquit, with lows around 38°F. Wrap up your sightseeing on the 9th (Sun) to allow time to drive to Boston.

Things to do in Ogunquit

Historic Sites · Tours · Breweries & Distilleries · Parks

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.
You'll find plenty of places to visit near Boston: Salem (The House of the Seven Gables, Salem Witch Museum, &more) and Dolphin & Whale Watching (in Gloucester). There's still lots to do: admire the natural beauty at Boston Public Garden, explore the world behind art at Museum of Fine Arts, walk around Boston Common, and take an in-depth tour of Boston Tea Party Ships & Museum.

Plan my day in Boston using traveler tips and tourist information provided by Inspirock.

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, plan for somewhat warmer nights in Boston, with lows around 50°F. Finish up your sightseeing early on the 15th (Sat) so you can go by car to Sandwich.

Things to do in Boston

Museums · Parks · Historic Sites · Outdoors

Side Trips

Sandwich

— 4 nights
Sandwich is a town in Barnstable County, Massachusetts, United States. You'll find plenty of places to visit near Sandwich: Nobska Point Lighthouse (in Woods Hole), Highfield Hall & Gardens (in Falmouth) and Stone Bridge Farm (in Acushnet). There's still lots to do: take an in-depth tour of Sandwich Glass Museum, contemplate the waterfront views at Cape Cod Canal, see the interesting displays at Heritage Museums & Gardens, and experience rural life at Coonamessett Farm.

Quickly create a custom-made itinerary for Sandwich using our trip planner.

Traveling by car from Boston to Sandwich takes 1.5 hours. Alternatively, you can take a bus. In October, plan for daily highs up to 64°F, and evening lows to 46°F. Finish your sightseeing early on the 19th (Wed) to allow enough time to drive to Provincetown.

Things to do in Sandwich

Museums · Outdoors · Wildlife · Tours

Side Trips

Provincetown

— 4 nights

Birthplace of American Liberty

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.
Explore Provincetown's surroundings by going to Nauset Beach (in Orleans) and Salt Pond Visitor Center (in Eastham). There's still lots to do: kick back and relax at Cape Cod National Seashore, do a tasting at Truro Vineyards of Cape Cod, examine the collection at Provincetown Art Association and Museum, and take a leisurely stroll along MacMillan Wharf.

To find more things to do, where to stay, and tourist information, read our Provincetown route planner.

You can drive from Sandwich to Provincetown in 1.5 hours. Another option is to take a bus. Expect a daytime high around 63°F in October, and nighttime lows around 49°F. Finish your sightseeing early on the 23rd (Sun) so you can fly to Newport.

Things to do in Provincetown

Outdoors · Parks · Beaches · Museums

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.
Get out of town with these interesting Newport side-trips: Foxwoods Resort Casino (in Mashantucket), Mystic Seaport Museum (in Mystic) and Lizzie Borden House (in Fall River). Next up on the itinerary: see the interesting displays at The Breakers, steep yourself in history at Marble House, cruise along Ocean Drive Historic District, and tour the old-fashioned way with a train tour.

To plan Newport vacation without wasting time, ask Inspirock to design an itinerary.

Traveling by flight from Provincetown to Newport takes 2 hours. Alternatively, you can drive; or do a combination of ferry and bus. In October in Newport, expect temperatures between 64°F during the day and 50°F at night. Finish your sightseeing early on the 27th (Thu) to allow enough time to fly to Bar Harbor.

Things to do in Newport

Historic Sites · Outdoors · Museums · Tours

Side Trips

Bar Harbor, Mount Desert Island

— 4 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Step out of Bar Harbor to go to Winter Harbor and see Schoodic Point, which is approximately 46 minutes away. The adventure continues: take in the awesome beauty at Cadillac Mountain, contemplate the waterfront views at Jordan Pond Path Trailhead, examine the collection at Maine Granite Industry Museum, and hike along Great Head Trail.

For traveler tips, reviews, maps, and other tourist information, use the Bar Harbor online trip planner.

Getting from Newport to Bar Harbor by flight takes about 3 hours. Other options: drive; or take a bus. Traveling from Newport in October, expect Bar Harbor to be a bit cooler, temps between 59°F and 42°F. Wrap up your sightseeing by early afternoon on the 31st (Mon) to allow enough time to fly back home.

Things to do in Bar Harbor

Parks · Outdoors · Nature · Trails

Side Trips