Northeast Road Trip From New York City

By Road Trip USA author Jamie Jensen

This road trip through the northeast winds along pastoral valleys and ancient mountains connecting three dynamic cities–New York, Boston and Montreal–while passing through quaint country retreats and revived Rust Belt towns. The landscapes are perhaps more varied than anywhere in the country: Cape Cod’s broad beaches, the rugged seascapes of Acadia, powerful Niagara Falls–joined together by endless hardwood forests that come alive with fall colors. There are also plenty of chances to sample regional food at roadside pancake houses, soft-serve ice cream stands, lobster pounds, and seafood shacks.

This itinerary assumes driving 200-400 miles a day; add more time if you want to linger or simply get out of the car more often. Note that all mileage estimates and driving times are approximate.

Starting Point: New York City
Total Driving Distance: ~2,300 miles
Suggested Trip Length: 14 days

Day 1

Driving Distance: ~200 miles
From New York City, follow the “Appalachian Trail” through the historic Hudson Valley to the bucolic vacation resorts of the Berkshires.

farmland surrounding a round building
Hancock Shaker Village. Photo © Reinout Van Wagtendonk/Dreamstime.


  • West Point: The U.S. Army’s famous military academy boasts a small museum, guided tours of the grounds, and scenic Trophy Point.
  • Norman Rockwell Museum: Take a stroll through the museum’s collection of Norman Rockwell’s art. The surrounding town of Stockbridge is worth exploring, too.
  • Hancock Shaker Village: Tour the living museum’s exhibits and see working artisans interpreting the rural lifestyle and famous design skills of the Shakers.

Overnight: Lenox, MA

Days 2-5

Driving Distance: ~300 miles
Connect with US-20 (“The Oregon Trail“) in Williamstown, then follow the scenic “Mohawk Trail” road east to Boston and Cape Cod.

calm water under a wooden bridge in concord Massachusetts
The Old North Bridge in Concord, MA. Photo © Thomas Brandt/Dreamstime.


  • Concord: Get a sense of the lives of four influential American writers: Ralph Waldo Emerson, Nathaniel Hawthorne, Henry David Thoreau, and Louisa May Alcott.
  • Boston: Visit a plethora of historical landmarks including the Old North Church and the Paul Revere House, or catch a game at Fenway Park.
  • Plymouth Rock: Like the Liberty Bell and Mt. Rushmore, it’s something every American tourist has to see.
  • Provincetown: Visit the Pilgrim Monument and Museum and admire the best panorama on the Cape.

Overnights: Concord, MA; Boston, MA; Provincetown, MA

Day 6-7

Driving Distance: ~400 miles
Return via New Bedford to I-95, then zoom north to Acadia National Park.

fountain with a waterfront in the distance
Bar Harbor’s waterfront. Photo © Mircea Dobre/Dreamstime.


  • New Bedford: Along with learning about the town’s whaling history, fan’s of Herman Melville can visit Seamen’s Bethel, which was featured in a chapter of the classic Moby Dick.
  • Lowell: Take a walking tour of Jack Kerouac’s hometown and learn about his life there.
  • Bar Harbor: Enjoy the most authentic lobster pound around at Thurston’s and browse in the town’s gift shops and art galleries.

Overnights: Lowell, MA, and Bar Harbor, ME

Day 8-10

Driving Distance: ~430 miles
From Acadia National Park, follow US-2 (“The Great Northern“) west across New Hampshire and Vermont to Montreal.

green ground cover on a mountaintop with a view of the water in maine
The scenic view atop Cadillac Mountain. Photo © Sharon Cobo/Dreamstime.


  • Cadillac Mountain: Experience a breathtaking panorama over Mount Desert Island, the surrounding inlets and islands, and the coast.
  • Mount Washington: Ascend the mountain to the summit and visit the historic Tip Top House.
  • Fairbanks Museum: This charming but quirky Victorian-era center of knowledge was established by Franklin Fairbanks in 1889 and hosts a fascinating array of oddities.
  • Ben & Jerry’s: Vermont’s number-one tourist attraction offers tours, a gift shop, and a variety of ice cream, frozen yogurt, and sorbet flavors.
  • Lake Champlain: Stroll along the boardwalk of Waterfront Park and take a sunset cruise on board the Spirit of Ethan Allen.

Overnights: Gorham, NH; Montpelier, VT; Montreal, QB

Days 11-14

Driving Distance: ~900 miles
From Montreal, journey via Ottawa to Niagara Falls, then follow US-20 (“The Oregon Trail“) to Cooperstown and back to New York City.

sunny day over a lake in mount royal park
Picturesque Mount Royal Park. Photo © Tempestz/Dreamstime.


  • Mount Royal Park: The park’s stairs and paths lead up to a belvedere, from which you will have a sweeping view of the city, the St. Lawrence River, and the southern suburbs.
  • Niagara Falls: Stand on the brink at Prospect Park or Goat Island or venture underneath the falls on a Maid of the Mist boat tour.
  • Erie Canal: South of Rochester, I-390 runs alongside one of the only still-intact sections of the original waterway.
  • Baseball Hall of Fame: Peruse a timeline of dioramas and display cases that walk you through the sport’s greatest—and most embarrassing—moments.

Overnights: Ottawa, QB; Buffalo, NY; Cooperstown, NY

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