If you're dreaming of a charming New England road trip, there are a number of routes you can take. The Green Mountain Byway promises a wildly scenic journey through Vermont's most famous towns. Meanwhile, this Massachusetts road trip along the coast is full of idyllic seaside spots
. But if you're looking for a route that traverses through multiple states in the U.S.' lovely northeastern corner, this road trip is for you.Seamlessly blending laidback beach villages, storied mountain towns, and vibrant
cities, this romantic route has everything you need for a well-rounded tour of New England. Looping through four states — Vermont, Massachusetts, Connecticut, and Rhode Island — the drive is perfect for sampling the region's most stunning sights. Stretching about 370 miles across New England, the journey can be completed in one day without stops. However, you'll definitely want to take your time and enjoy the stops along the way. After all, it's all about the journey, not the destination.
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Manchester, Vermont
The route begins in Manchester, Vermont, whose nearest airports are Albany International Airport roughly 63 miles away and Burlington International Airport about 100 miles away. After renting a car, drive past picturesque Vermont communities and gorgeous Green Mountain scenery until you reach Manchester's small-town embrace.
A shopper's dream come true, Manchester hosts a delightful mix of boutiques and designer retail shops. Take a stroll along Main Street, where you'll find local treasure troves like Northshire Bookstore and adorable art galleries like Catbird Studio. For a post-shopping bite, pop into Charlie's Coffee House for a fresh-baked pastry or a specialty sandwich. Or, for heartier fare, step into Ye Olde Tavern. Downtown Manchester is also home to Pastime Pinball, a vintage pinball museum with over 60 colorful, flashing machines that are free to play.
For history buffs, a visit to Hildene is a must. The stunning early 20th-century mansion was once home to Robert Lincoln, the son of Abraham and Mary Todd Lincoln. Tour the 412-acre estate outfitted with over a dozen historic buildings, gorgeous gardens, and a historic carriage barn that now houses The Museum Store. General admission is $25, which includes a self-guided tour of the Georgian Revival home decorated to reflect the bygone era.
Stockbridge, Massachusetts
Leaving the green mountains of Vermont, continue about 80 miles south to Stockbridge, a small but mighty Massachusetts mountain town in the Berkshires. There, you'll be exposed to a wonderland of historic buildings, such as Norman Rockwell's former art studio — a 19th-century carriage barn that has since been converted into the Norman Rockwell Museum. The beloved American artist spent his golden years in Stockbridge, inspiring one of his most renowned paintings, "Home for Christmas (Stockbridge Main Street at Christmas)," which is on permanent display at the museum.
If you're feeling inspired by Rockwell's nostalgia-filled depiction of the town's Main Street, step out of the studio and onto the streets of downtown Stockbridge. Stroll past historic homesteads like the Colonial-period Mission House and the late 1800s Sedgwick House, which was home to one of Stockbridge's oldest families. Afterward, visit the Sedgwick family plot at the Stockbridge Cemetery, which also serves as Rockwell's final resting place.
You'd be remiss if you stayed anywhere else in Stockbridge than the Red Lion Inn (no, not the popular hotel chain). Dating back to 1773, the historic inn's antique-adorned rooms have hosted luminaries from every era, including Paul Newman, James Taylor, Eleanor and Theodore Roosevelt, Nathaniel Hawthorne, Buster Keaton, and many more. While you're there, be sure to dine at The Main Inn, the property's historic formal restaurant that sparkles under crystal chandeliers.
New Haven And Mystic, Connecticut
Next up: Connecticut. Situated about 80 miles south of Stockbridge is the state's historic college town, New Haven. Home to the illustrious Ivy League institution Yale University, New Haven is a smart stop filled with arts and culture. Visit the Yale University Art Gallery to admire over 300,000 works of art, many of which date back centuries. Then, stroll over to the Yale Peabody Museum to marvel at impressive natural history exhibits on everything from dinosaurs to Ancient Egypt.
Off campus, bite into New Haven's renowned food scene with a slice of apizza — the city's distinctive thin-crusted, coal-fired pizza that rivals New York City's. Established in 1925, Frank Pepe Pizzeria is one of the oldest pizza joints in town, serving up fresh slices of specialty pies like the original tomato pie with mozzarella and the white clam pizza.
Save room for a second slice. The next stop on the route is Mystic, a small town on the scenic Connecticut coast that boasts a film-famous pizzeria. Opened in 1973, Mystic Pizza is a family-owned restaurant with so much charm that there's a whole movie centered around it. Starring Julia Roberts, the 1988 romantic comedy "Mystic Pizza," put Mystic on the map, and its namesake eatery is an essential stop for foodies and movie buffs alike. Beyond pizza, Mystic brims with maritime attractions such as the Mystic Seaport Museum. Featuring a bounty of historic vessels, the museum houses the world's last wooden whaling ship, the Charles W. Morgan. After visiting the museum, walk through Historic Seaside Village, which is lined with 19th-century homes and buildings.
Providence, Rhode Island
Situated about 50 miles northeast of Mystic, Providence awaits. Hailed as one of the quirkiest cities in America, this vibrant capital gives you plenty of unique things to do. For literature lovers, a visit to the Providence Athenaeum is a must. There, you can walk in the hallowed footsteps of Edgar Allan Poe and H.P. Lovecraft while browsing shelves of 19th-century books. If you're a fan of Lovecraft in particular, you can even visit his last residence at 65 Prospect Street and his final resting place at Swan Point Cemetery.
Providence is also well known for its thriving arts scene, boasting dozens of galleries selling local artwork and sprawling venues like The WaterFire Arts Center. A simple stroll downtown will expose you to an abundance of public art displays, including award-winning sculptures and colorful murals. For a trip down one of the most charming cobblestone streets in America that will transport you back in time, take a walk down Benefit Street. The mile-long stretch is dotted with historic buildings such as The Nightingale-Brown House, which dates back to 1792.
Be sure to sample the city's delicious food scene while you're there. Ranked fifth on Food & Wine's list of "America's next great food cities," Providence is bursting with flavorful destinations. For fresh seafood favorites and riverside dining, reserve a table at Hemenway's Seafood Grill & Oyster Bar. Or, for a casual retro dining experience, head to Haven Bros Diner. What began as a humble horse-drawn cart has been transformed into a burger-slinging mobile restaurant. Operating into the wee hours of the morning, it's the perfect spot for a late night bite.
Cape Cod, Massachusetts
Heading east from Providence, your charm-filled New England road trip concludes in Massachusetts along the Cape Cod peninsula. Comprising nearly 560 miles of captivating coastline, Cape Cod is brimming with shorefront spots. Some of the most beautiful beaches are nestled along the Cape Cod National Seashore, a 40-mile coastal corridor dotted with seaside gems like the popular Coast Guard Beach in Eastham and Cape Cod's oldest lighthouse, the Highland Light in Truro.
Of course, you'd be remiss to sleep on the seafood in Cape Cod. With five locations scattered throughout the region, Mac's Seafood is a fan favorite, renowned for fresh fish, succulent lobster, and broiled cod. If you want to make your own meal, pop into Mac's Seafood Market next to the Provincetown location. Also in Provincetown, The Lobster Pot has been revered as the town's prime chowder spot since 1979, serving up piping hot bowls of award-winning New England clam chowder.
To conclude your journey, check into a quaint bed and breakfast like The Captain Farris House in South Yarmouth. Dating back to 1845, the historic home flaunts Greek Revival architecture, idyllic gardens, period-decorated guest rooms, and an adorable afternoon tea room. From there, you can take a day trip to Martha's Vineyard, the iconic American island that captures the charm of an English village.
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