Celebrate America’s 250th anniversary with a road trip from Boston to Philadelphia with stops at sites important to the founding of America and early American History. From the Boston Tea Party protesting “taxation without representation” and the signing of the Declaration of Independence during the Revolutionary War to the inauguration of George Washington, America’s first president, and the Statue of Liberty, travel down the East Coast on this road trip to partake in 2026 festivities and merrymaking.
This road trip spans about 316 miles from Boston, Massachusetts, to Philadelphia, Pennsylvania. We recommend taking 12 to 15 days on this journey to fully enjoy all the stops along the way. We’ve listed the Choice Hotels on the route, where, as a AAA Member, you can save 10% or more on standard hotel rates while earning Choice Privileges points.
Stop 1 - Boston
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Known as the birthplace of the American Revolution, Boston is a fitting stop on a road trip celebrating the 250th birthday of the United States. Even when it's not a notable anniversary, the city proudly celebrates its place in American history and its part in the war for independence from England.
During your stay in Boston, walk the Freedom Trail, visiting notable stops like the Old State House, Faneuil Hall and the Paul Revere House. The trail terminates at the Bunker Hill Monument, which commemorates the Battle of Bunker Hill, the first major battle of the American Revolutionary War. If you are up for the challenge, end your journey on the Freedom Trail by climbing the steps to the top of the obelisk for views of Boston from every direction.
Other must-see things to do in Boston include the Boston Tea Party Ships and Museum, where visitors learn about the Boston Tea Party in 1773 when members of the Sons of Liberty protested the taxes levied in the Tea Act by boarding an East India Company ship in the cover of night and dumping over 300 crates of tea overboard into the harbor.
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Stop 2 - Hartford, CT
100 miles - about 2 hours and 15 minutes
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Depart Boston and head to Hartford, Connecticut, where you can visit historical sites, an amusement park and an art museum. Schedule a historical tour at the Stowe Center for Literary Activism to see the house where Harriet Beecher Stowe, author of “Uncle Tom's Cabin,” lived to learn more about Stowe and the abolitionist movement to end slavery in the U.S.
Head to the Mark Twain House and Museum to see the beautiful Victorian home where Twain lived with his wife and children from 1874 to 1891. And don't miss The Wadsworth while in Hartford. The museum first opened in the mid-19th century and today displays a collection of European, American and contemporary art.
Lastly, thrill seekers can head to Six Flags New England for a mix of family rides and thrill rides, including roller coasters. If you prefer water parks, go to Six Flags Hurricane Harbor for splash pads and water slides.
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Stop 3 - New Haven, CT
40 miles - about 45 minutes
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Head south back toward the coastline to stop in New Haven, a town founded in 1638 by English Puritans. The Connecticut city sits on the shores of the Long Island Sound, near New York, and is home of Yale University, founded in 1701.
Take a free tour of the Yale Campus to learn about its history and architecture. After your one-hour tour, visit one or more of the museums on Yale’s campus, like the Yale Peabody Museum for natural history or the Yale University Art Gallery for artwork ranging from ancient to contemporary.
Off campus, learn about New Haven’s history at the New Haven Museum with temporary and permanent exhibits, including an exhibit on the Amistad Rebellion. You may know about it from the 90s Steven Spielberg film “Amistad,” but the museum does a deep dive into the details of the 1839 rebellion, ranging from when 53 West African people took over the ship from a crew intending to sell them into slavery, to how they won back their freedom during a trial in New Haven.
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Stop 4 - Stamford, CT
42 miles - about 50 minutes
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Spend time outdoors in Stamford, our next stop on a road trip celebrating the 250th birthday of the U.S. Enjoy some of the town’s outdoor spaces at parks, gardens and an arboretum.
On over 80 acres of land, the Stamford Museum & Nature Center has nature trails; a working farm with cows, pigs and chickens among other animals; a vegetable garden; a planetarium and more. Nearby, Bartlett Arboretum and Gardens has hiking trails on its nearly 100 acres of trees and gardens. Best of all, the arboretum is free to visit.
Among Stamford's notable beaches are Cummings Park Beach, Cove Island Beach and West Beach. While the steep parking fees for nonresidents is prohibitive for some visitors, these stretches of coastline continue to attract beachgoers.
Stop 5 - New York City
40 miles - 1 hour and 15 minutes
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Follow the coastline south and take part in many of the iconic things to do in New York City. Watch a Broadway play, eat all kinds of food (not just bagels, pizza and pastrami sandwiches, though those are delicious), get lost in a museum and more.
For America's 250th anniversary, though, reserve a spot on the ferry to visit the Statue of Liberty. Lady Liberty, dedicated in 1886, was a gift from France and has stood as a symbol of American freedom, the abolishment of slavery and a beacon of hope to immigrants seeking a better life. After your time at the Statue of Liberty, the ferry will take you to Ellis Island, where you can tour the processing center that some 12 million immigrants passed through before it closed in 1954.
Other historical sites include Federal Hall National Memorial, where George Washington was sworn into office during his first inauguration.
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Stop 6 - Philadelphia
95 miles - about 2 hours
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Philadelphia, the sixth and final stop on this road trip to celebrate America's 250th anniversary, was founded in 1682 and is the birthplace of America's independence. The First and Second Continental Congresses were held in Philadelphia. It's where the Continental Army was first formed and where the Founding Fathers signed the Declaration of Independence on July 4, 1776, declaring America's independence from England. It was even the capital of the United States before Washington, D.C.
In a city brimming with American history, Independence Hall National Historical Park is a can't-miss attraction. The park has many sites, with some ticketed and others free. One you should definitely reserve your tickets for in advance is Independence Hall, where the Declaration of Independence was signed. While in the park, also spend time at the Benjamin Franklin Museum, the Liberty Bell, Congress Hall and more.
Another must-do is a visit to the Museum of the American Revolution. The exhibits here detail America’s path to independence, teaching visitors about events that led to the Revolutionary War, the war itself and America as a newly founded nation.
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Though this is the end of this journey, you can continue the road trip south, stopping at places like Washington, D.C., Great Smoky Mountains National Park in North Carolina and Tennessee, and Charleston, South Carolina.