Family Road Trips in the Northeast United States
With a pandemic raging on, many of us have been confined within our homes for the last few months. Forget elaborate vacations—it’s been a while since some of us even got a coffee from the café down the street! As states begin opening up, we’re starting to explore the possibility of leaving our homes. While we aren’t quite ready to jet off to a busy, all-inclusive resort in a tropical location, we may be ready to plan a little road trip close to home. If you’re based in or around Boston and are looking for a short drive perfect for a long weekend, check out this post.
But if you think part of the fun is getting there, check out some of the fun places you can explore around and just beyond New England! Spend a week exploring hidden gems close to home, having a family singalong, and enjoying each other’s company without distance learning, zoom calls, or the confining walls of the home you haven’t left in months.
Of course, your options vary depending on where you live. Whether you live near New England or not, you could always make this trip part of a longer itinerary, but for me, Boston is my home, so that’s where I’m starting.
Northern New England
Manchester, VT to Burlington, VT to Stowe, VT to North Conway, NH to Portland, ME
As the birthplace of America, New England is full of history and diverse cultures that many of us don’t take the opportunity to explore. The northern states especially are famous for their lakes, mountains, and quiet, quaint rural life, making them perfect for a relaxed road trip.
During your drive, bask in the rolling hills, tall mountains, streams and rivers, and—if you go later in the fall—the famous foliage. For a taste of history along the way, stop at any of the roadside inns (many of which even pre-date the American Revolution!), and enjoy a tall glass of a local craft beer. If you or your little ones get bored during the drive, enjoy a time-honored travel tradition: counting cows!
Manchester, VT
(3 Hours from Boston)
A quaint, picturesque town between the Green Mountains and the Taconic Range, Manchester is known for its cottages and country inns. A great destination for those fond of outdoor activities, the town offers skiing in winter and hiking in summer. Take a moment to breathe in the fresh outdoor air, gaze at the green grass and luscious foliage, or stroll through one of the shops downtown. Manchester is home to one of my favorite bookstores!
Burlington, VT
(2 Hours 20 min from Manchester)
A college town on the shore of Lake Champlain and just south of the Canadian border, Burlington is the largest city in Vermont. Home to several local arts and music scenes, the city has a variety of interesting shows all year around, including one performed by the House of LeMay, Burlington’s own drag troupe.
If water sports are more your speed, check out sailing, canoe, and kayaking lessons at Waterfront Park, picnic or enjoy a barbecue at North Beach Park, or visit the Lake Champlain Dragon Boat Festival, an annual charity boat race that supports Burlington’s cancer survivors.
Stowe, Vermont
(45 min from Burlington)
Stowe is famed as “The Ski Capital Of The East”. True to its name, it is a favorite destination of skiers and home to the Stowe Mountain Resort, a famous ski resort with terrain on Spruce Peak and Mount Mansfield. You can stay for a while at Smuggler’s Notch or—my personal favorite—the Trapp Family Lodge. Apart from skiing, you can go hiking and horseback riding in summer, and kids can enjoy a variety of sports and kid-friendly activities.
North Conway, NH
(2 Hours 20 min from Stowe)
North Conway is a charming New Hampshire village tucked between soaring mountain peaks and dense forests, making it perfect for families who love the ourdoors. You can ski, hike, or rock climb, then slow things down at Echo Lake State Park with swimming, boating, or fishing.
For something a little different, hop aboard a vintage train at the historic Victorian rail station with the Conway Scenic Railroad, browse the nearby outlets, or—our family favorite—challenge yourselves at Monkey Trunks, an aerial obstacle course.
Portland ME
(1 Hour 30 min from North Conway)
Portland may be Maine’s largest city—and home to the biggest seaport in New England—but it still feels wonderfully authentic. I love walking along the waterfront, breathing in the salty sea air as I watch the fishermen bring in their latest catch. Nearby, the Old Port district pairs vibrant nightlife with beautiful 19th-century architecture.
For visitors, Portland has everything—and I mean everything: museums and art galleries, parks and libraries, concert venues and lighthouses, wineries and breweries, incredible seafood, golf courses, and plenty of perfect picnic spots. You can cruise the islands of Casco Bay, catch a performance by the Portland Symphony Orchestra at Merrill Auditorium, and—of course—eat your way through a farm-to-table dining scene that’s put this small city back on the map.
Southern New England
Providence, RI to Newport, RI to Mystic, CT to Lenox, MA
While Northern New England is known for rugged peaks and ski terrain, Southern New England shines with gentle hills, scenic meadows, and accessible hiking trails. Add in charming coastlines, calm sailing waters, and classic beach days, and the south offers a softer, seaside take on outdoor adventure.
Providence RI
(1 Hour from Boston)
Located at the mouth of the Providence River at the head of Narragansett Bay, Providence is known for its ethnic neighborhoods (get some great Italian food on Federal Hill!), community organizations, and arts associations. You and your family can visit the historic churches, the museums, as well as the city’s extensive park system. Personally, we love the nearby Roger Williams Zoo!
Newport RI
(45 Min from Providence)
Another must-visit road trip spot in Rhode Island is Newport. Often called the “Sailing Capital of the World,” Newport invites you to get out on the water and explore its stunning coastline by boat. On land, history takes center stage—from grand Gilded Age mansions and some of the oldest taverns in the country to the Touro Synagogue, the oldest standing synagogue in America.
Mystic, CT
(1 Hour from Newport)
Then there’s Mystic, a charming seaside village in Connecticut. The town is packed with inviting restaurants—many serving standout seafood—along with unique attractions like the Mystic Aquarium, home to marine life you won’t see at most aquariums. Step back in time with cruises aboard vintage sailing ships and classic steamboats, and you’ll quickly see why Mystic is a favorite for travelers who love history, coastal charm, and a slower pace.
Lenox, MA
(2 Hours from Mystic)
Your final stop is Lenox, a historic town in the heart of Massachusetts’ Berkshires. As home to the Boston Symphony Orchestra and Shakespeare & Company, Lenox is a dream destination for theater and music lovers alike. Beyond the stage, you can explore the Berkshire Scenic Railway Museum with its historic train exhibits or head outdoors to Pleasant Valley Wildlife Sanctuary, which offers nature trails, summer camps, seasonal programs, and hands-on educational experiences for both kids and adults year-round.
Upstate New York
Albany, NY to Lake George, NY to Woodstock, VT
When you hear the words “New York,” the first thing that jumps to your mind is New York City, but I actually prefer visiting the small towns upstate over the Big Apple.
The region is home to a vast rural area, which supports a strong agricultural and dairy industry. But it’s also home to famous scenic sights like Niagara Falls, Finger Lakes, the Adirondack Mountains, and the Catskills (Dirty Dancing, anyone?).
Take a minute to admire crystal-clear lakes, rivers, expansive caverns, and explore state parks, historic forts, and a variety of museums along the way.
Albany NY
(2 Hours 45 Min from Boston)
Then there’s Albany, a city rich in history, culture, and striking architecture. Along with a lively nightlife scene filled with restaurants, bars, and entertainment, Albany also offers plenty of green space with parks and recreation areas woven throughout the city.
At the heart of it all is Empire State Plaza, a collection of state buildings that showcase the city’s Dutch and English colonial roots. Highlights include the awe-inspiring New York State Capitol and the historic Albany City Hall, both must-sees for visitors interested in New York’s past.
Lake George NY
(1 Hour from Albany)
Located in Warren County, New York, along the shores of Lake George, is a town of the same name. The area is a favorite for families, offering everything from water sports and paddling to camping, hiking, amusement parks, and even factory outlet shopping! Just around the corner is Queensbury, home to one of America’s oldest annual hot air balloon festivals.
Within the town of Lake George itself, you’ll find charming hamlets and historic forts that add a touch of history to this outdoor-focused destination.
Woodstock, VT
(2 Hours from Lake George)
Woodstock, Vermont is a charming year-round destination set along the Ottauquechee River at the crossroads of the Vermont Byway. Nestled in the Green Mountains of Windsor County, Woodstock is home to Vermont’s only national park and three historic covered bridges, making it a beautiful place to experience New England’s most fabulously-colorful falls and outdoor activities.
Families will love a stop at Billings Farm & Museum, where kids can explore a working dairy farm, meet the famous Jersey cows, and even milk a cow themselves! Woodstock also features a delightful local science museum, adding an extra layer of learning and discovery to your visit.
Oh Canada!
Burlington, NY to Montreal to Quebec to Portland, ME
If you’re up for a longer drive—and a passport stamp—head north to Canada. You’ll be rewarded with a distinct culture, stunning architecture, and a food scene that feels surprisingly European.
To break up the journey, plan a night in Burlington, Vermont, about three hours away. Then, continue on toward the border to begin the next leg of your adventure.
Montreal
(2 Hours from Burlington)
Spend time strolling through Mont-Royal, the city’s iconic park, where sweeping views from the summit reveal Montréal spread out below you. In Old Montréal, cobblestone streets and buildings dating from the 17th to the 19th centuries offer a glimpse into the city’s French colonial roots. Don’t miss the Montréal Botanical Garden (Jardin botanique), home to 10 greenhouse exhibitions and 30 beautifully themed gardens showcasing plants from around the world. One of my personal favorites is Notre-Dame Basilica—Montréal’s oldest church—which comes alive each evening with an incredibly unforgettable light show.
Quebec City
(3 Hours from Montreal)
One of the most famous tourist destinations in the country is Quebec City, located in the French-speaking province of Quebec. Quebec is ideal for strolling around, popping into shops, and experiencing the local cuisine. If you’re looking for historic happenings, atop the Cap Diamat is the La Citadelle de Québec, a massive historic fortress that the kids can run around.
Plus, the Plains of Abraham (Champs de Bataille) are perfect for picnics. You can even hop aboard the Québec-Levis Ferry, which offers an unrivaled view of the city skyline!
Portland ME
(5 Hours from Quebec)
See above
THE U.S. HISTORY TOUR
Plymouth, MA to Philadelphia to Washington D.C. to New York City
If quaint towns aren’t quite your style, consider a different kind of road trip: a history hike! Or, well…drive. While larger cities may take longer to fully open due to their higher population density, they offer an unmatched depth of historical context. For a true deep dive into early American history, begin in Plymouth to learn about the earliest settlers, then continue on to Philadelphia to experience the stories and sites that shaped the Revolutionary era.
Philadelphia PA
(5 Hours from Pymouth)
Philadelphia is a city in the state of Pennsylvania, known for its role in the American Revolution. Follow the Historic American Revolution Trail of Philadelphia starting at the Museum of the American Revolution, located in the heart of Philadelphia’s Historic District. Continue onto Carpenter’s Hall (where the first Continental Congress met), the Graff House (where the Declaration of Independence was written) and to Independence Hall (where it was signed).
If all that history makes you hungry, enjoy a famous Philly cheesesteak before departing for Washington, D.C.!
Washington DC
(2 Hours 30 Min from Philadelphia)
Washington, D.C. is home to some of the most significant historical sites in the country. From iconic monuments to powerful memorials and world-class museums, history is everywhere you turn, and all of it’s worth exploring. As the country begins to reopen, there’s something especially meaningful about experiencing the city that holds so many artifacts representing both our nation’s greatest challenges and its proudest moments. You could spend days in the Smithsonian Museum alone!
New York City
(4 Hours from Washington DC)
On your return, spend a few nights in New York City, the cultural, financial, and media capital of the world. Experience the progress our nation has made with a visit to Ellis Island to learn how immigrants made our country what it is today. NYC is also home to some of the best restaurants, bars, nightclubs, museums, libraries, universities and colleges, and media centers in the entire world. New York City has something for the whole family, from history buffs to the family’s resident foodie.
Whew, that was a lot! Whether you’re looking to stay close to home or collect a few passport stamps with an international road trip (once the pandemic is over, of course), book a FREE Dream Trip Chat so I can help you take a break from the busy.
Who is Christina?
Meet Christina Vieira, a Traveler, a Planner, and a Mom. She is also the owner of Showcase the World Travel, a modern travel agency that helps busy Moms take the vacation they deserve without adding “planning it all” to their to-do lists. After all, Mom should get to enjoy their vacation, too!
She specializes in Disney, the Caribbean, and Europe, and has helped dozens of families have magical vacations that they will always remember. She loves traveling with her four-year-old, Annabelle. Her favorite destinations include Walt Disney World, Wyoming, and Prague.
