Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

Philadelphia to Freeport Maine 4-Day Rail/Train Trip

Viewed by 120 travelers

Day 1: Exploring Philadelphia

Philadelphia, PA, USA

8:00AM

Visit Liberty Bell

Start your day by visiting the iconic Liberty Bell and learn about its historical significance.
Walk or take a short taxi ride from your accommodation to Liberty Bell Center.
Free, 1-2 hours

12:00PM

Lunch at Reading Terminal Market

Enjoy a variety of delicious food options at the bustling Reading Terminal Market.
Walk from Liberty Bell to Reading Terminal Market.
$$, 1 hour

3:00PM

Explore Philadelphia Museum of Art

Admire art collections and don't miss running up the famous 'Rocky Steps' for a great view.
Take a short taxi or public transport to the museum.
$, 2-3 hours

7:00PM

Dinner at Rittenhouse Square

Indulge in a lovely dinner at one of the restaurants around the charming Rittenhouse Square.
Take a taxi or walk to Rittenhouse Square for dinner.
$$$, 2 hours
Find Hotels in Philadelphia

Day 2: New York City Exploration

New York City, NY, USA

9:00AM

Visit Times Square

Experience the vibrant atmosphere of Times Square with its bustling streets and dazzling billboards.
Take an Amtrak train from Philadelphia to New York City.
Free, 2 hours

12:00PM

Lunch at Chelsea Market

Savor a variety of gourmet food options at the popular Chelsea Market.
Walk or take a taxi to Chelsea Market.
$$, 1-2 hours

3:00PM

Explore Central Park

Take a leisurely stroll or rent a bike to explore the beautiful Central Park.
Walk or take public transport to Central Park.
Free, 2-3 hours

7:00PM

Dinner at a Broadway Restaurant

Enjoy dinner at a restaurant near Broadway and maybe catch a show afterwards.
Walk or take a taxi to a restaurant near Broadway.
$$$, 2-3 hours
Find Hotels in New York City

Day 3: Boston Sightseeing

Boston, MA, USA

9:00AM

Freedom Trail Tour

Embark on a guided tour of the famous Freedom Trail to learn about Boston's history.
Take an Amtrak train from New York City to Boston.
$, 3 hours

12:00PM

Lunch at Quincy Market

Enjoy a variety of food options at Quincy Market, a historic marketplace in Boston.
Walk from Freedom Trail to Quincy Market.
$$, 1 hour

3:00PM

Visit Fenway Park

Explore the iconic Fenway Park, home of the Boston Red Sox, and take a stadium tour.
Take public transport or a short taxi ride to Fenway Park.
$$, 2-3 hours

7:00PM

Dinner at North End

Dine at one of the charming Italian restaurants in Boston's North End neighborhood.
Take a taxi or walk to North End for dinner.
$$$, 2 hours
Find Hotels in Boston

Day 4: Exploring Freeport, Maine

Freeport, ME, USA

9:00AM

Visit LL Bean Flagship Store

Start your day exploring the iconic LL Bean Flagship Store and shop for outdoor gear.
Take a train or bus from Boston to Freeport, Maine.
Free, 1-2 hours

12:00PM

Lunch at Linda Bean's Maine Kitchen

Enjoy delicious seafood and local cuisine at Linda Bean's Maine Kitchen.
Walk from LL Bean Flagship Store to Linda Bean's Maine Kitchen.
$$, 1 hour

3:00PM

Explore Wolfe's Neck Woods State Park

Take a nature walk and enjoy the beautiful coastal scenery at Wolfe's Neck Woods State Park.
Take a short taxi ride or walk to Wolfe's Neck Woods State Park.
$, 2-3 hours

7:00PM

Dinner at Harraseeket Inn

Indulge in a fine dining experience at the elegant Harraseeket Inn.
Take a taxi or walk to Harraseeket Inn for dinner.
$$$, 2 hours
Find Hotels in Freeport
0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version
Itinerary created by AI-assisted, human-reviewed

Plan Your Philadelphia to freeport Maine Trip

Cost Estimator
Estimate your trip budget
Packing List
Get a custom checklist
Weather Expert
Check weather & best time to go