Exploring New England on a Shoestring Budget Road Trip

Day 1: City Exploration

Boston, Massachusetts

8:00AM

Freedom Trail

Start your day with a walk along the historic Freedom Trail in Boston, visiting landmarks like the Paul Revere House and Faneuil Hall.
Begin at Boston Common and follow the red-brick trail throughout the city.
$0, 3 hours

12:00PM

Quincy Market

Indulge in a variety of affordable food options at Quincy Market for lunch.
Located in Faneuil Hall Marketplace.
$10, 1 hour

2:00PM

Harvard University

Take a stroll around Harvard University's campus in nearby Cambridge.
Drive or take public transportation to Harvard Square.
$0, 1.5 hours

6:00PM

Dinner at Union Oyster House

End your day with a classic seafood dinner at the historic Union Oyster House.
Located on Union Street in Boston.
$20, 1.5 hours
View Hotel Availability

Day 2: Coastal Charm

Portland, Maine

9:00AM

Portland Head Light

Drive to Cape Elizabeth to explore the iconic Portland Head Light and enjoy stunning ocean views.
About a 20-minute drive from Portland city center.
$0, 2 hours

12:00PM

Lunch at Central Provisions

Savor a delicious and affordable lunch at Central Provisions in the heart of Portland.
Located on Fore Street.
$15, 1 hour

2:00PM

Old Port District

Explore the charming Old Port district with its cobblestone streets, boutique shops, and local cafes.
Walk around Exchange Street and Commercial Street.
$0, 2 hours

6:00PM

Dinner at Eventide Oyster Co

Indulge in fresh, budget-friendly seafood dishes at Eventide Oyster Co.
Located on Middle Street.
$25, 1.5 hours
View Hotel Availability

Day 3: Mountain Adventure

White Mountains, New Hampshire

8:00AM

Franconia Notch State Park

Embark on a hike to the stunning Flume Gorge or take the aerial tramway at Cannon Mountain for breathtaking views.
Head to Franconia Notch State Park, about a 2-hour drive from Portland.
$16, 4 hours

1:00PM

Picnic Lunch

Enjoy a picnic amidst the scenic beauty of the White Mountains.
Find a picturesque spot within the state park.
$10, 1 hour

3:00PM

Kancamagus Highway Scenic Drive

Take a leisurely drive along the Kancamagus Highway, renowned for its fall foliage and natural beauty.
Start from Lincoln and head east on Route 112.
$0, 2 hours

7:00PM

Dinner at Black Mtn Burger Co

Enjoy delicious and affordable burgers at Black Mtn Burger Co in Lincoln.
Located on Main Street.
$12, 1 hour
View Hotel Availability

Day 4: Scenic Drive

Green Mountains, Vermont

9:00AM

Drive through Green Mountain National Forest

Embark on a picturesque drive through the lush Green Mountains, stopping at scenic overlooks for photos.
Start the drive from the town of Manchester.
$0, 4 hours

1:00PM

Lunch at Up for Breakfast

Fuel up with a hearty breakfast-for-lunch at Up for Breakfast in Manchester.
Located on Main Street.
$15, 1 hour

3:00PM

Bennington Museum

Explore the rich history and art at the Bennington Museum in the charming town of Bennington.
Drive to Bennington from Manchester.
$12, 2 hours

7:00PM

Dinner at Papa Pete's

Enjoy affordable and delicious Italian cuisine at Papa Pete's in Bennington.
Located on North Street.
$18, 1.5 hours
View Hotel Availability

Day 5: Cultural Exploration

Berkshires, Massachusetts

9:00AM

Norman Rockwell Museum

Discover the iconic American illustrator's work at the Norman Rockwell Museum in Stockbridge.
Drive to Stockbridge from Bennington, VT.
$20, 3 hours

1:00PM

Lunch at Haven Cafe & Bakery

Enjoy a cozy lunch at the Haven Cafe & Bakery in Great Barrington.
Located on Railroad Street.
$12, 1 hour

3:00PM

Tanglewood Music Center

Stroll the picturesque grounds of Tanglewood, the summer home of the Boston Symphony Orchestra, in Lenox.
Drive to Lenox from Great Barrington.
$0, 2 hours

7:00PM

Dinner at Six Depot Roastery & Cafe

Enjoy a farm-to-table dinner at Six Depot in West Stockbridge.
Located on Main Street.
$25, 1.5 hours
View Hotel Availability

Day 6: Coastal Relaxation

Newport, Rhode Island

9:00AM

Cliff Walk

Embark on the scenic Cliff Walk, offering breathtaking views of the Atlantic Ocean and historic Newport mansions.
Start at the 40 Steps entrance on Narragansett Avenue.
$0, 2 hours

12:00PM

Lunch at Cappy's Chowder House

Savor a seafood lunch at Cappy's Chowder House in downtown Newport.
Located on West Marlborough Street.
$20, 1 hour

2:00PM

Newport Mansions Tour

Explore the opulent Gilded Age mansions like The Breakers or Marble House for a glimpse into Newport's history.
Choose a mansion to tour and purchase tickets on-site.
$25, 2 hours

7:00PM

Dinner at Salvation Cafe

Indulge in Caribbean-inspired cuisine at Salvation Cafe in Newport.
Located on Broadway.
$20, 1.5 hours
View Hotel Availability