All Articles 5 essential East Coast road trips

5 essential East Coast road trips

These scenic routes make the case for taking things slow.

Kate Templin Stahl
By Kate Templin Stahl2 Mar 2023 4 minutes read
Historic buildings on Chalmers Street in Charleston, South Carolina
Historic buildings on Chalmers Street in Charleston, SC
Image: Peter Unger/Getty Images

In today’s world, we place much importance on getting places quickly. Why walk when you can drive, find a cab when you can call an Uber, or take back roads when expressways exist? If we could all hit pause though, we’d realize that sometimes the slow route is the best one—especially when it comes to these five East Coast road trips.

On these spectacular drives, you’ll discover must-see scenery, sites, and towns, all while enjoying the journey in between. From a charming tour of New England to a Southern sojourn, these itineraries will inspire you to hit the open road at your own pace.

St. Augustine, FL, to Charleston, SC

Oak lined path in Charleston, South Carolina
Oak lined path in Charleston, SC
Image: Bonnie Cameron/Getty Images

This road trip begins in the nation’s oldest city, St. Augustine, established in 1565 on Florida's northeast coast. The Spanish-influenced town features a mix of historic architecture, lovely beaches (notably in Anastasia State Park), the kitschy “Fountain of Youth,” and a plethora of ghost tours inspired, of course, by the city’s impressive age.

From St. Augustine, drive up to one of the south’s most iconic destinations, Charleston, SC, by way of Savannah, GA. The two cities are connected by US-17, a beautiful stretch of road that passes a number of horse farms and historic churches—keep an eye out for the Old Sheldon Church Ruins, the site of an 18th-century church that was burned during both the Revolutionary and Civil wars.

Once you reach Charleston, check into the Emeline, a boutique hotel conveniently located next to the Historic Charleston City Market. For dinner, head to favorite King Street seafood spot 167 Raw Oyster Bar. Arrive early to put your name on the list, as the restaurant doesn’t take reservations, and grab a drink around the corner at the restaurant's newly opened sister spot, Bar 167, while you wait for a table.

Boston to Acadia National Park, Maine

Portland Head Light, Cape Elizabeth, Maine
Cape Elizabeth, Maine
Image: Ekkachai Pholrojpanya/Getty Images

After exploring Boston’s best attractions, from Faneuil Hall and Boston Common to the swan boats in the Public Garden, start the 285-mile trip north on U.S. Route 1 to Acadia National Park in Maine. Your first stops on the drive should be Gloucester, MA, to see the lighthouses and fishermen memorials, and then Rachel Carson National Wildlife Refuge, a 9,125-acre park located along 50 miles of Maine's southern shore.

Make a detour on State Route 9 to Kennebunkport, Maine, to ogle the 400-year-old town’s stunning mansions and dine on fresh Maine lobster, then return to Route 1 and continue on to Portland, Maine. Grab a room at the Blind Tiger, a new guesthouse in a 19th-century home, and get a good night’s sleep.

The next day, make the three-hour scenic journey along the coast to Acadia. The 47,000-acre national park features views of rocky beaches and granite peaks like Cadillac Mountain, the highest point on the East Coast, along with the chance to spot moose, bear, and whales.

Washington, D.C., to Nags Head, NC

Lynnhaven Inlet, Virginia Beach, Virginia
Lynnhaven Inlet, Virginia Beach, VA
Image: Sky Noir Photography by Bill Dickinson/Getty Images

Start this tour in our nation’s capital, taking in the memorials and museums (many of which are free to visit), before heading 280 miles south to the Outer Banks of North Carolina. From D.C., you’ll follow the interstate south to Fredericksburg, VA, where you’ll switch to Routes 3 and 17. The two meandering roads, known together as the Tidewater Trail, wind along the oyster-filled Rappahannock and cross the York and James rivers, which empty into the Chesapeake Bay.

Continue to North Carolina, crossing the Wright Memorial Bridge into the town of Nags Head. Here, you’ll find towering sand dunes at Jockey’s Ridge State Park, salt marshes at Nags Head Woods Preserve, and the still-working Bodie Island Lighthouse, which dates to the 1870s and offers sweeping views of Cape Hatteras National Seashore. Dine at seafood shack Sam and Omie’s, open since 1937, and rest your head at The Sanderling, an oceanfront resort with all the charm of a boutique hotel.

Miami to Key West, FL

Sunrise on the beach in Key West, Florida
Sunrise on the beach in Key West, FL
Image: Crawford A. Wilson III/Getty Images

Florida’s Overseas Highway—a 107-mile stretch that connects the southern part of Miami, near Everglades National Park, to Key West—is best driven slowly, with plenty of stops to sightsee, swim, and feast on conch fritters and mahi mahi sandwiches at spots like waterfront dive Alabama Jacks in Key Largo. John Pennekamp Coral Reef and Bahia Honda state parks are also must-sees en route. The latter spans a full 524 acres and boasts some of Florida’s best beaches.

After crossing the narrow, seven-mile bridge into Key West, check into Casa Marina or The Reach. The sister Curio Collection by Hilton properties are both located on quiet beaches that are just a short walk to the party on Duval Street.

Vermont’s Route 100

Aerial view of Stowe, Vermont
Aerial view of Stowe, VT
Image: marchello74/Getty Images

Route 100 stretches almost the entire length of Vermont, traveling for more than 200 miles through beautiful New England countryside. Along the way, charming towns like Wilmington, Warren, and Stowe offer country stores, farm stands, and yes, a lot of maple syrup.

Plan for stops at Fat Toad Farm in Brookfield to watch goat’s milk caramel being made, and the no-frills Mad Taco in Waitsfield for carnitas tacos made with pork shoulder that's house smoked for 12 hours. Once you’re full, take the scenic, 14-mile Green Mountain Byway to Stowe, where you can bed down at the family- and dog-friendly Lodge at Spruce Peak. For something a bit swankier, try the Pitcher Inn, a Relais & Châteaux property in nearby Warren.

Kate Templin Stahl
Kate Stahl is a Chicago-based journalist and essayist who has written for POPSUGAR, Chicago Tribune, and various Modern Luxury publications, among others. She also co-hosts and produces a podcast called My Mom Always Says.