Driving from Boston to D.C.: Your One-Way Guide

Let us recommend the top places to stop on your drive from Boston to Washington DC to make for the perfect New England road trip.

For an unforgettable vacation full of history, culture, winding roads and lovely scenery, begin driving from Boston on your one-way trip to our nation’s capital. After flying into Boston Logan International Airport, spend some time in one of the oldest cities in America. Boston, or “Beantown,” has cobblestone roads, die-hard Red Sox fans and incredible lobster rolls, which make it the perfect place to start an exciting journey south.

The driving distance between Boston and Washington, D.C., is roughly 440 miles and can be completed in slightly less than eight hours. However, with a one-way car rental, you can easily stretch this drive into a five- to seven-day vacation. Here’s a guide to assist you as you drive and discover this culturally rich region — at your own pace.

Boston and Beyond

Drive to the heart of Beantown and park in the garage beneath Boston Common.  Upstairs you’ll find the first stop of the Freedom Trail. Walk the 2.5-mile trail to come upon 16 historical sites including museums, churches, graveyards, memorials and downtown attractions like Faneuil Hall. The centuries-old marketplace is right on the waterfront and offers a wide variety of food, including local favorites like clam chowder and shepherd’s pie.

Faneuil Hall Hungry travelers should look no further than Quincy Market at Faneuil Hall for a taste of Boston.

Head southwest from downtown toward Kenmore Square to explore the other side of Boston at Fenway Park. If you’re a fan, grab some Red Sox gear and snap a photo with the Green Monster—the green left-field wall at Fenway that ranks as the tallest wall of any current Major League Baseball park— before driving across the Charles River via the Boston University Bridge and venturing into Cambridge. Take a tour of Harvard University, or spend the afternoon exploring Harvard Square’s shops like the quirky Black Ink gift store, eateries like Russell House Tavern, and music and theater venues like Brattle Theatre.

After exploring Boston, drive an hour west on Interstate 90 and stop at Old Sturbridge Village, where you can experience rural New England life as it was at the turn of the 19th century. The largest living museum in New England, this village is full of antique buildings, machinery and costumed actors who’ll make your visit as entertaining as it is educational.

Got extra time? From Boston, you can also deviate from the main route to explore the fall foliage of New England and the Northeast on one of many amazing autumnal drives, like the less than 2-hour route east along the coast to Hyannis Port in Cape Cod. Pack a picnic and spend an afternoon at Keyes Beach, or drive onto the Steamship Authority ferry, which brings passengers and vehicles to the charming New England island known as Martha’s Vineyard.

Connecticut Through Pennsylvania

As you make your way south through Connecticut, stop in New Haven for the town’s staple dish, apizza — a thin, doughy, chewy-crusted take on the classic dish that’s pronounced “ah-BEETs.” Head to Frank Pepe Pizzeria, a local favorite since 1925, which is known for its original white clam pizza.

If you’re not in a rush, hop on the Merritt Parkway for the scenic route. Drive through forests and under architecturally unique overpasses all the way to Greenwich, Connecticut, before getting back on Interstate 95 south toward the Big Apple.

Whether visiting New York is on your bucket list or not, the city is right in the middle of your vacation route and offers a ton to see and do. Stop for a day or three and wave to Lady Liberty, feel the breeze atop the Empire State Building and catch a show like “Phantom of the Opera” on Broadway or Shakespeare in Central Park. Tip: avoid driving through traffic in Manhattan by leaving your car at a Park-and-Ride and catching a lift into the city.

Continue through New Jersey until you reach the City of Brotherly Love, Philadelphia. Visit the Liberty Bell and tour Independence Hall — where the U.S. Declaration of Independence and the Constitution were debated and signed. Then drive to the south side of town for one of the city’s best-known eats, a Philly cheesesteak from Tony Luke’s.

Liberty Bell An iconic symbol of American independence, the Liberty Bell’s inscription reads: “Proclaim Liberty Throughout All the Land Unto All the Inhabitants Thereof.”

Got extra time? Before crossing over the Pennsylvania border, stop in the Brandywine Valley to spend the afternoon sipping local wines and browsing artisan crafts on the Brandywine Valley Wine Trail, then stay the night in one of the area’s quaint bed-and-breakfast spots, like the Kennett House.

Delaware Through the District

Roll down your windows and enjoy the view as you drive over the Delaware River via the Delaware Memorial Bridge. Continue on I-95 to Maryland, where you’ll take Exit 53 and follow signs to Baltimore’s Inner Harbor. Park in Harbor Park Garage and head into the National Aquarium to see — and even touch — some of its more than 16,000 sea creatures and coastal land dwellers, like dolphins, puffins, jellyfish, sloths and American bullfrogs.

Afterward, hop on a harbor boat cruise or water taxi, or rent paddle boats designed to look like a monster named Chessie, the Chesapeake Bay’s take on Nessie, the Loch Ness monster. For dinner, drive just a mile northwest to Lexington Market. Try some of Maryland’s famous crab, or whatever you fancy, from this historical Baltimore institution featuring more than 100 food vendors and serving up local food since 1782.

Then drive an hour south to your final destination: Washington, D.C. Spend at least a day on the National Mall exploring monuments and the Capitol and stopping in Smithsonian museums like the National Museum of Natural History and the National Air and Space Museum. Before going home, make sure you catch a sunset while dining on the Georgetown waterfront and see a show at The Kennedy Center for the Performing Arts.

National Mall Discover more than 10 museums, the Capitol, Washington Monument, Lincoln Memorial (above) and other nationally recognized symbols by spending a day at the National Mall.

Got extra time? Before heading into D.C., take a detour to Fort McHenry, where the Battle of Baltimore was fought during the War of 1812. Inspired by the famous battle, Francis Scott Key penned what is now known as “The Star-Spangled Banner,” the U.S. national anthem.

Heading Home

It’s simple. Return your rental vehicle to any of the three airports in the Washington, D.C., area.

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Driving from Boston?

Rent a car at Boston Logan International Airport!

About the Author

Lisa Zimmermann is a Washington, D.C.-based writer and has previously written for Boston magazine, Boston HomeBoston WeddingsThe Dallas Morning NewsThe Jersey JournalNew England Travel and Atlas Magazine. She’s resided in multiple points along this one-way route including Boston, New York City, Jersey City and Washington, D.C. Follow her on Twitter @lisazimm or Instagram @lzloveslife.