Ready for one seriously epic East Coast road trip?
This Virginia to Maine route takes you from the Mid-Atlantic all the way to the rocky coast of New England, with mountain hikes, famous historic sites, and busy waterfronts.
Along the way, you can climb to sweeping viewpoints, walk streets that helped shape American history, explore grand mansions, see centuries-old lighthouses, and eat more than a few lobster rolls.
The full route covers hundreds of miles, but the stops are close enough to keep driving days manageable and leave plenty of time for exploring.
Keep reading for the best stops, must-do activities, scenic drives, hiking trails, and practical tips for planning an unforgettable Virginia to Maine road trip.
1. Richmond, Virginia
Richmond, Virginia’s capital, sits along the James River in the central part of the state, about 2 hours from Washington, D.C.
Start at the Virginia State Capitol, designed by Thomas Jefferson and completed in 1788, then explore the nearby American Civil War Museum for stories and artifacts from the Civil War era.
For outdoor fun, head to Belle Isle, a 54-acre island where walking trails, river views, and huge sunbathing rocks offer a fun break from your road trip.
Before driving north toward Maine, stroll Monument Avenue, check out colorful murals around the Arts District, or grab lunch in historic Church Hill.
The neighborhood is home to St. John’s Church, where Patrick Henry gave his famous “Give me liberty, or give me death!” speech in 1775.
2. Shenandoah National Park, Virginia
Drive about 1.5 hours to Shenandoah National Park, where the Blue Ridge Mountains stretch across nearly 200,000 acres of western Virginia.
Drive the 105-mile Skyline Drive, which follows the mountain ridgeline and features more than 75 overlooks, including Spitler Knoll Overlook and Range View Overlook.
Stretch your legs on the 1.4-mile round-trip Dark Hollow Falls Trail, which drops about 440 feet to a 70-foot waterfall, or climb Hawksbill Mountain, the park’s highest point at 4,051 feet.
Shenandoah also protects over 500 miles of hiking trails, including 101 miles of the Appalachian Trail, so keep an eye out for black bears and white-tailed deer before continuing north toward Maine.
3. Philadelphia, Pennsylvania
It’s time to explore city streets in Philadelphia, Pennsylvania, located about 3.5 hours from the national park and right along the Delaware River.
Start at Independence Hall, where the Declaration of Independence was adopted in 1776 and the U.S. Constitution was signed in 1787, then walk across the street to see the 2,080-pound Liberty Bell.
Next, tackle the 72 famous steps at the Philadelphia Museum of Art, snap a photo with the Rocky statue, and wander through Reading Terminal Market, which has served hungry locals since 1893.
Before heading farther north, order a cheesesteak at Pat’s King of Steaks or Geno’s Steaks, then stroll Elfreth’s Alley, a cobblestone lane dating to 1703 with 32 historic homes.
4. Cold Spring, New York
Leaving Philadelphia behind, drive about 2 hours and 30 minutes to Cold Spring, a small Hudson River village in New York with mountain views and a walkable 19th-century Main Street.
Browse the antique shops and cafés along Main Street, then wander down to Cold Spring Waterfront for views across the Hudson to Storm King Mountain.
If you’re ready to hike, take the Cornish Estate Trail, an easy route through the woods that leads to the ruins of the historic Cornish Estate.
For something easier, explore the 90-acre West Point Foundry Preserve, where trails pass ruins from an ironworks that produced cannons, steam engines, and other machinery during the 1800s.
5. Mystic, Connecticut
Continue roughly 2.5 hours to Mystic, Connecticut, a small coastal village on the Mystic River that built hundreds of wooden sailing ships during the 1800s.
Mystic Seaport Museum should be your first stop, which holds more than 650 historic watercraft, including the 1841 Charles W. Morgan, the world’s oldest surviving wooden whaling ship.
Next, meet beluga whales, African penguins, and thousands of other marine animals at Mystic Aquarium, then watch the Mystic River Bascule Bridge rise to let boats cruise through downtown.
Save room for a slice at Mystic Pizza, the restaurant that inspired the name of the 1988 Julia Roberts movie, or grab fresh seafood before you leave.
6. Newport, Rhode Island
Follow the coast about an hour’s drive to Newport, Rhode Island, a sailing city famous for enormous Gilded Age mansions and sweeping Atlantic Ocean views.
Tour The Breakers, a 70-room Vanderbilt mansion completed in 1895, then follow the 3.5-mile Cliff Walk past crashing waves and estates like Marble House and Rosecliff.
Hop back in the car for the 10-mile Ocean Drive, which loops past rocky shoreline, historic Fort Adams, and Brenton Point State Park, a favorite spot for watching colorful kites soar above the water.
Before continuing toward Maine, explore the shops and restaurants along Thames Street and Bowen’s Wharf, where you can grab a lobster roll while sailboats cruise through Newport Harbor.
7. Boston, Massachusetts
Next, drive about 1.5 hours to Boston, Massachusetts, where Revolutionary War landmarks, legendary sports, and some seriously good food pack plenty into one road trip stop.
Follow the 2.5-mile Freedom Trail to 16 historic sites, including Boston Common, Paul Revere’s House, the Old North Church, and the USS Constitution, launched in 1797.
Then head to Fenway Park, home of the Boston Red Sox since 1912, or browse more than 100 shops and food spots around Faneuil Hall Marketplace and Quincy Market.
Before pointing the car toward Maine, stroll the cobblestone streets of Beacon Hill, snap a photo along Acorn Street, and grab a cannoli from Mike’s Pastry.
8. Portland, Maine
After Boston, cruise about 2 hours to Portland, Maine, a waterfront city on Casco Bay where working fishing boats share the harbor with ferries, restaurants, and historic brick buildings.
Explore the cobblestone streets of the Old Port, then visit the Portland Museum of Art, home to more than 20,000 artworks by names like Winslow Homer, Claude Monet, and Andy Warhol.
Drive about 20 minutes to Portland Head Light in Cape Elizabeth, first lit in 1791 and surrounded by the 90-acre Fort Williams Park.
Finish your day back on the waterfront with a Maine lobster roll, or hop aboard a Casco Bay Lines ferry for an island cruise before your road trip continues up the coast.
9. Acadia National Park, Maine
For the grand finale, drive about 3 hours to Acadia National Park, where 49,000 acres of mountains, forests, rocky coastline, and lakes cover much of Maine’s Mount Desert Island.
Cruise the 27-mile Park Loop Road to reach Sand Beach, Thunder Hole, and Jordan Pond, then walk the 3.3-mile Jordan Pond Path around clear water framed by the rounded Bubbles mountains.
For a bigger adventure, hike the Beehive Loop, which features steep granite staircases, iron rungs, and exposed cliff faces, or choose one of Acadia’s 45 miles of historic carriage roads for an easier outing.
End your road trip atop 1,530-foot Cadillac Mountain, the highest point on the eastern U.S. coastline, where wide Atlantic views make one seriously memorable finish.