History, harbors, and quintessential fall foliage.
History, harbors, and quintessential fall foliage.
Boston, MA 02108Stark, NH 03582
Trip overview
Journey through the heart of American history, from Boston's revolutionary cobblestones to the charming maritime spirit of Portland, Maine. This road trip winds through ivy-clad campuses, scenic coastal byways, and rolling hills ablaze with autumn color, offering a perfect blend of historical landmarks and culinary delights.
Day-by-day itinerary
Day 1 — Boston
The Freedom Trail
Walk this iconic 2.5-mile red-brick path through downtown Boston, which passes 16 nationally significant historic sites. Start at Boston Common and trace the steps of revolutionaries, visiting landmarks like the Massachusetts State House and Paul Revere's House.
139 Tremont St, Boston, MA 02108
Faneuil Hall Marketplace
A historic meeting hall dubbed the "Cradle of Liberty," now a bustling marketplace with shops, street performers, and the Quincy Market Colonnade, offering dozens of food stalls. It's a vibrant hub of history and modern city life.
4 S Market St, Boston, MA 02109
Giacomo's Ristorante
Experience an authentic Italian dinner in Boston's historic North End at this famously popular, cash-only spot. The bustling atmosphere and delicious, generously portioned pasta dishes make the inevitable wait worthwhile.
355 Hanover St, Boston, MA 02113
The Liberty, a Luxury Collection Hotel
Stay in a stunningly reimagined historic building that was once the Charles Street Jail. This unique luxury hotel offers a memorable blend of history, sophisticated design, and modern comfort at the foot of Beacon Hill.
215 Charles St, Boston, MA 02114
Day 2 — Cambridge
Harvard University Campus Tour
Walk through the historic Harvard Yard, the oldest part of America's oldest university. Admire the iconic ivy-covered brick buildings, rub the foot of the John Harvard statue for good luck, and soak in the academic atmosphere of this world-renowned institution.
1350 Massachusetts Ave, Cambridge, MA 02138
Salem Witch Trials Memorial
A solemn and moving outdoor memorial dedicated to the victims of the 1692 witch trials. Stone benches are inscribed with each victim's name, providing a quiet space for reflection on this dark chapter of American history.
24 Liberty St, Salem, MA 01970
Strawbery Banke Museum
Explore over 300 years of American history in this 10-acre outdoor living history museum. Wander through historic homes on their original foundations, interact with costumed role-players, and watch traditional crafts being demonstrated.
14 Hancock St, Portsmouth, NH 03801
Hotel Portsmouth
Check into a beautifully restored 1881 Queen Anne Victorian mansion, now a chic boutique hotel. It offers a perfect blend of historic charm and modern amenities, located just a short walk from Portsmouth's vibrant Market Square.
40 Court St, Portsmouth, NH 03801
Day 3 — York
Nubble Lighthouse
One of America's most iconic and photographed lighthouses, perched on a rocky island just off the coast of York. While the lighthouse itself isn't accessible, Sohier Park offers fantastic views, especially at sunrise or sunset.
Sohier Park Rd, York, ME 03909
The Clam Shack
Grab a classic Maine lobster roll from this legendary seafood stand right on the Kennebunk River. Known for its fresh-picked lobster meat served on a toasted round bun, it's a quintessential, no-frills New England summer experience.
2 Western Ave, Kennebunk, ME 04043
Old Port
Explore the heart of Portland with a walk through the Old Port's charming cobblestone streets. This historic district is packed with 19th-century brick buildings that now house unique boutiques, art galleries, and acclaimed restaurants.
Commercial St, Portland, ME 04101
Portland Regency Hotel & Spa
Stay in a historic 19th-century armory in the heart of the Old Port. This hotel combines classic architecture with modern luxury, providing an elegant and convenient base for exploring Portland's waterfront and downtown.
20 Milk St, Portland, ME 04101
Day 4 — Cape Elizabeth
Portland Head Light
Visit Maine's oldest lighthouse, commissioned by George Washington and first lit in 1791. Set in the beautiful Fort Williams Park, the iconic white tower sits on a rocky headland, offering breathtaking views of Casco Bay.
12 Captain Strout Cir, Cape Elizabeth, ME 04107
Portland Museum of Art
Discover an impressive collection spanning from American and European masters to contemporary works, with a special focus on artists from Maine like Winslow Homer and Andrew Wyeth. The museum is housed in a collection of beautiful historic and modern buildings.
7 Congress Sq, Portland, ME 04101
Eastern Promenade
Take a relaxing walk or drive along this 68-acre waterfront park designed by the Olmsted Brothers. It offers panoramic views of Casco Bay and its islands, a sandy beach, and beautiful walking trails.
Eastern Promenade, Portland, ME 04101
Eventide Oyster Co.
A modern and lively oyster bar that has redefined the New England seafood restaurant. Enjoy an incredible selection of fresh, local oysters and an innovative Brown Butter Lobster Roll that breaks from tradition in the most delicious way.
86 Middle St, Portland, ME 04101
Day 5 — Lincoln
Kancamagus Highway
Drive a spectacular 34.5-mile section of Route 112 through the heart of the White Mountain National Forest. This designated National Scenic Byway is world-famous for its incredible fall foliage, with numerous scenic overlooks, hiking trails, and waterfalls along the way.
NH-112, Lincoln, NH 03251
Artist's Bluff Trail
Hike this relatively short but rewarding 1.5-mile loop trail for one of the most iconic views in New England. The rocky ledge at the top provides a stunning panorama of Echo Lake and the surrounding Franconia Notch mountains.
Franconia Notch Pkwy, Franconia, NH 03580
Stark Covered Bridge
Capture the quintessential New England photo at this charming covered bridge, built in 1862. This picturesque 'paddleford' truss bridge spans the Ammonoosuc River and is set against the backdrop of a quaint village church, making it a perfect final stop.
N Stark Rd, Stark, NH 03582
Experiences & guides
Bookable tours and stops worth a detour along this route.
Experiences
Guide content may not reflect current conditions. Always verify information before your trip.
Frequently asked questions
The New England History road trip covers about 299 mi and roughly 7h 43m of driving, comfortably spread across about 5 days.
This itinerary maps out 19 stops from Boston, MA 02108 to Stark, NH 03582. Highlights include The Freedom Trail, Nubble Lighthouse, and Portland Head Light.
It begins in Boston, MA 02108 and ends in Stark, NH 03582, following a mapped, road-following route the whole way.
The estimated cost is around $1,933, covering fuel, lodging, food, and activities. Your actual total varies with the season, your pace, and the choices you make along the way.
Open New England History in the free Road Trip app for turn-by-turn navigation, the full day-by-day itinerary, live weather, and gas-cost tracking along the route.
More road trips
Open this trip in the app
Take this route with you — navigation, live weather, and gas tracking inside Road Trip.
