Whether it’s your first trip to New England or you vacation here every year, these itineraries will help you explore charming seaside towns and bustling cities, eat at cutting-edge restaurants and the best seafood shacks, and experience both popular spots and hidden gems. Mix and match the itineraries, or use them as a jumping-off point for your own adventure.
Cape Cod Beaches and Villages, 7 Days
Cape Cod can be all things to all visitors, with quiet villages and lively resorts, gentle bayside wavelets and crashing surf. A car is the best way to meander along Massachusetts’s beach-lined, arm-shape peninsula, but in busy town centers—such as Falmouth, Hyannis, Chatham, and Provincetown—you can get around easily on foot. Keep in mind that Cape-bound traffic is particularly bad on Friday afternoon–evening and Saturday morning–afternoon (most house rentals are Saturday to Saturday), and traffic in the other direction is rough on Sunday, especially in the afternoon. Cross as early in the day as possible or wait until evening. For most visitors, time at the beach is key, but there is plenty to do and see once you’ve had enough sun and surf or if the weather doesn’t cooperate. And about those beaches: be prepared to pay for day passes—most beach parking lots charge a sometimes-hefty fee.
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Fly in: Logan International Airport (BOS), Boston
Fly out: Logan International Airport (BOS), Boston
Day 1: Hyannis
The best way to spend a week on the Cape is to pick a central location and use it as a launching point to explore. Begin by crossing the Bourne Bridge and head east on U.S. 6 toward Hyannis: make this centrally located, larger town your headquarters.
The crowded Mid Cape is a hive of activity, and its heart is Hyannis. Here you can cruise around the harbor or go on a deep-sea fishing trip. There are shops and restaurants along Main Street and plenty of kid-friendly amusements. Fans of John F. Kennedy shouldn’t miss the museum in his honor. End the day with a concert at the Cape Cod Melody Tent (open seasonally) or the Cotuit Center for the Arts.
Day 2: Falmouth
For your first excursion, wander along Route 28 until you reach Falmouth in the Upper Cape. Here you can stroll around the village green, duck into some of the historic houses, and stop at the Waquoit Bay National Estuarine Research Reserve for a walk along the barrier beach. Take some time to check out the village of Woods Hole, a center for international marine research, and the year-round ferry port for Martha’s Vineyard. A small aquarium has regional sea-life exhibits and touch tanks. If you have extra time, head north to the lovely old town of Sandwich, known for the Sandwich Glass Museum, and the beautiful grounds and collection of antique cars at Heritage Museums and Gardens.
Logistics: 21 miles; via Rte. 28 N; 48 minutes, starting in Hyannis.
Day 3: Barnstable, Yarmouth Port, Dennis
Spend your day exploring the northern reaches of the Mid Cape with a drive along scenic Route 6A, which passes through the charming, slow-paced villages of Barnstable, Yarmouth Port, and Dennis. There are beaches and salt marshes, antiques shops and galleries, and old cemeteries along this route. Yarmouth Port’s Bass Hole Boardwalk makes for a particularly beautiful stroll. In Dennis there are historic houses to tour, and the Cape Cod Museum of Art merits a stop. End the day by climbing 30-foot Scargo Tower to watch the sun set. At night you can catch a film at the Cape Cinema, on the grounds of the Cape Playhouse.
If you’re traveling with kids, spend some time in the southern sections of Yarmouth and Dennis, where Route 28 passes by countless amusement centers and miniature-golf courses.
Logistics: 9 miles; via Rte. 6A E; 20 minutes, starting in Hyannis.
Day 4: Chatham
Chatham, with its handsome Main Street, is a perfect destination for strolling, shopping, and dining. A trip to the nearby Monomoy Islands is a must for bird-watchers and nature lovers. Back in town visit the many inviting galleries and restaurants, stop by the Atwood House Museum, and drive over to take in the view from Chatham Light.
Logistics: 19½ miles; via U.S. 6 E; 35 minutes, starting in Hyannis.
Day 5: Cape Cod National Seashore
On Day 5, leave your Hyannis hub and head for the farther reaches of Cape Cod. Take U.S. 6 east, before making a slight detour onto the less commercial end of Route 28. On the way north toward Orleans you’ll drive past sailboat-speckled views of Pleasant Bay.
Stop in Eastham at the Cape Cod National Seashore’s Salt Pond Visitor Center. Take time to stroll along one of the beaches—there are more than 40 miles of pristine sand from which to choose—or bike on the many picturesque trails. Head slightly farther north to historic Marconi Station, which was the landing point for the transatlantic telegraph early in the 20th century, or park your car in Wellfleet‘s historic downtown area, where you’ll find a bounty of intriguing shops and galleries. It’s also worth walking the short but stunning White Cedar Swamp Trail. Continue on to Provincetown to spend two nights at the tip of the Cape.
Logistics: 47 miles; via U.S. 6 E; 1¼ hours, starting in Hyannis.
Days 6 and 7: Provincetown
Bustling, LGBTQIA-popular Provincetown sits at the very end of the Cape, and there’s a lot to see and do here. You can park the car and forget about it until you leave town, as everything is easily walkable. Catch a whale-watching boat and take a trolley tour through town, or bike through the Cape Cod National Seashore on its miles of trails. Climb the Pilgrim Monument for a spectacular view of the area—on an exceptionally clear day you can see the Boston skyline. Visit museums, shops, and art galleries, or spend the afternoon swimming and sunning on the beaches at Herring Cove or Race Point.
Logistics: 116 miles; via U.S. 6 W, Rte. 3 N and I–93 N; 2½ hours, starting in Provincetown and ending in Boston.
New Haven, Providence, and Boston in 5 days
These three cities offer some of the best dining in the Northeast, and each makes a case for having the finest Italian cuisine in the region, leaving you to judge whose cuisine reigns supreme. In addition, history buffs can get their fill while exploring New England’s Colonial and maritime past.
Fly in: Bradley International Airport (BDL), Hartford
Fly out: Logan International Airport (BOS), Boston
Day 1: New Haven
Start your journey in New Haven, Connecticut. The Constitution State’s second-largest city is home to Yale University, named for British shipping merchant Elihu Yale. Take an hour-long walking tour with one of the university’s guides and feast your eyes on the iconic Gothic-style structures that adorn the campus. After you’ve worked up an appetite, a stop for New Haven–style pizza is a must. Less than a mile from campus are two institutions known for thin-crust pies cooked in brick ovens: Pepe’s Pizzeria and Sally’s Apizza. For the burger enthusiast, there’s Louis’ Lunch on Crown Street. Don’t ask for ketchup; it’s been taboo here since they opened in 1895. Spend your first night in New Haven.
Logistics: 53 miles; via I–91 S; 1 hour staring at Bradley airport.
Day 2: New Haven to Providence
On your second day, get an early start, and head north on Interstate 95 toward Providence, Rhode Island. There are plenty of small towns bursting with New England’s maritime history along Connecticut’s shoreline. Stop in Niantic, New London, or Stonington and explore the region’s rich seafaring history. If you’re planning on making one stop on the way to Rhode Island, the seaside village of Mystic is worth at least a half day to explore the seaport or to take a boat out on the water. Mystic Seaport, with its nearly 500 ships and more than 60 preserved historic buildings, will transport you back to 19th-century New England. For those looking to try their luck at a game of chance, take a slight detour north on Interstate 395 to either of Connecticut’s two casinos, Foxwoods Resort Casino or Mohegan Sun. Overnight in Providence or in any of the seaside towns along the way.
Logistics: 103 miles; via I–95 N; 1 hour 45 minutes, starting in New Haven.
Day 3: Providence
Rhode Island’s capital holds treasures like Benefit Street, with its Federal-era homes, and the RISD Museum of Art at the Rhode Island School of Design. Be sure to savor a knockout Italian meal on Atwells Avenue in Federal Hill—Pane e Vino is a popular choice. For dessert, it’s hard to top the cannoli at Scialo Bros. Bakery. If you’re visiting in early June, sample authentic eats from all over Italy, while live music fills the streets, during the Federal Hill Stroll. During the warmer months, typically April–December, Providence hosts WaterFire, a public celebration of art and performance. The festival’s 100 bonfires on the rivers of downtown Providence attracts tens of thousands of viewers each year for the popular event. Spend the night in a downtown Providence hotel for easy access to sights and restaurants.
Days 4 and 5: Boston
A short drive north on Interstate 95 will bring you to Boston, New England’s cultural and commercial hub. To savor Boston’s centuries-old ties to the sea, take a half-day stroll past Faneuil Hall and Quincy Market or a boat tour of the harbor (you can even head out on a whale-watching tour from here). In Boston, famous buildings such as Faneuil Hall are not merely civic landmarks, but national icons. From the Boston Common, the 2.5-mile Freedom Trail links treasures of America’s struggle for independence, such as the USS Constitution (better known as “Old Ironsides”) and Old North Church (of “one if by land, two if by sea” fame). Be sure to walk the gas-lighted streets of Beacon Hill, too. Boston’s North End is the oldest residential neighborhood in the city, and has great dining options like Antico Forno, which offers pizza baked in a wood-burning brick oven.
The following day, either explore the massive Museum of Fine Arts and the grand boulevards and shops of Back Bay, or visit colorful Cambridge, home of Harvard University and the Massachusetts Institute of Technology (MIT). Lively Harvard Square is a perfect place to do some people-watching or catch a street performance; the All Star Sandwich Bar is an excellent choice for lunch. For an experience unique to the Boston area, head a few miles south of the city along U.S. 1 to Dorchester’s Boston Bowl to cap off your trip with candlepin bowling. Here, at all hours of the night, Bay Staters play a smaller version of 10-pin bowling that uses balls weighing less than 3 pounds and allows participants to bowl three balls per frame instead of two.
Logistics: 50 miles; via I–95 N and I–93 N; 1 hour, starting in Providence.
Massachusetts, New Hampshire, and Maine, 7 Days
Revel in the coastal beauty of three New England states—Massachusetts, New Hampshire, and Maine—on the path from the region’s largest city, Boston, to its highest peak, Mt. Washington. An assortment of New England’s treasures are at your fingertips as you negotiate the ins and outs of the jagged northeastern coastline, before ascending the heights of the White Mountains.
Fly in: Logan International Airport (BOS), Boston
Fly out: Logan International Airport (BOS), Boston
Day 1: The North Shore and New Hampshire Coast
After flying into Boston, pick up a rental car and head for the North Shore of Massachusetts. In Salem, the Peabody Essex Museum and the Salem Maritime National Historic Site chronicle the evolution of the country’s early shipping fortunes. Spend some time exploring more of the North Shore, including the old fishing port of Gloucester, and Rockport, a great place to find that seascape rendered in oils. Newburyport, with its Federal-style ship-owners’ homes, is home to the Parker River National Wildlife Refuge, beloved by birders and beach walkers.
New Hampshire fronts the Atlantic for a scant 18 miles, but it’s a pretty drive up the coast to quiet Odiorne Point State Park in Rye, through the charming village of New Castle, and into urbane and historic Portsmouth, where pre-Revolutionary high society built Georgian- and Federal-style mansions—visit a few at the Strawbery Banke Museum. Stay the night in Portsmouth at one of its inviting historic hotels, such as the centrally located Hotel Thaxter.
Logistics: 64 miles; via I–95 N; 1 hour 10 minutes, starting at Logan airport.
Day 2: The Yorks
Much of the appeal of the Maine Coast lies in geographical contrast—from its long stretches of swimming and walking beaches in the south to the rugged, rocky cliffs in the north. As the shoreline physically evolves, each town along the way reveals a slightly different character, starting with York.
In York Village take a leisurely stroll through the buildings of the Museums of Old York getting a glimpse of 18th-century life in this gentrified town. Spend time wandering between shops or walking nature trails and beaches around York Harbor. There are several grand lodging options here, most with views of the harbor. If you prefer a livelier pace, continue on to York Beach, a haven for families with plenty of entertainment venues. After taking in the view of Nubble Light, stop at The Goldenrod for a seaside lunch or dinner.
Logistics: 10 miles; via I–95 N; 15 minutes, starting in Portsmouth.
Day 3: Ogunquit and the Kennebunks
For well over a century, Ogunquit has been a favorite vacation spot for those looking to combine the natural beauty of the ocean with the sophistication of fine art galleries and restaurants. Take a morning walk along the Marginal Way to see the waves crashing against the rocks. In Perkins Cove, have lunch, stroll the shopping areas, or sign on with a lobster-boat cruise to learn about Maine’s most important fishery—the state’s lobster industry satisfies more than 80% of the nation’s appetite.
Head north to the Kennebunks, allowing at least two hours to wander through the shops and historic homes of Dock Square in Kennebunkport. This is an ideal place to rent a bike and ramble around backstreets, head out Ocean Avenue past large mansions, or ride to one of several beaches to relax awhile. Spend your third night in Kennebunkport.
Logistics: 22 miles; via I–95 N and Rte. 9 E; 30 minutes, starting in York.
Days 4 and 5: Portland
There’s enough to keep you happily busy for several days in Portland, Maine’s largest city. Explore its historic neighborhoods, shop and eat at the many hip, indie boutiques and restaurants in Old Port and elsewhere in town, and visit one of several excellent museums. A brief side trip to Cape Elizabeth takes you to Portland Head Light, Maine’s first lighthouse, which was commissioned by George Washington in 1787. The lighthouse is on the grounds of Fort Williams Park and is an excellent place for a picnic; be sure to spend some time wandering the ample grounds. There are also excellent walking trails (and views) at nearby Two Lights State Park. If you want to take a boat tour while in Portland, get a ticket for Casco Bay Lines and see some of the islands that dot the bay. Spend two nights in Portland.
Logistics: 28 miles; via I–95 N; 40 minutes, starting in Kennebunkport.
Day 6: Bretton Woods
Wake up early and drive to Bretton Woods, New Hampshire, where you’ll spend nights six and seven. It’s about a three-hour drive from Portland, much of it along windy, scenic roads. Drive northwest along U.S. 302 toward Sebago Lake, a popular water-sports area in the summer, and continue on toward the time-honored New England towns of Naples and Bridgton. Just 15 miles from the border of New Hampshire, and nearing Crawford Notch, U.S. 302 begins to thread through New Hampshire’s White Mountains, passing beneath brooding Mt. Washington before arriving in Bretton Woods.
Logistics: 98 miles; via Rte. 113 N and U.S. 302 W; 3 hours, starting from Portland.
Day 7: The White Mountains
In Bretton Woods, the Mount Washington Cog Railway chugs to the summit, and the Omni Mount Washington Resort recalls the glory days of White Mountain resorts. Beloved winter activities here include snowshoeing and skiing on the grounds; you can even zipline. Afterward, defrost with a cup of steaming hot cider while checking out vintage photos of the International Monetary Conference (held here in 1944), or head to the Cave, a Prohibition-era speakeasy, for a drink.
Logistics: 159 miles; via I–93 S; 2½ hours, starting at the Omni Mount Washington Resort and ending in Boston.
Maine’s Coast: Portland to Acadia National Park, 6 Days
Lighthouses, beaches, lobster rolls, and water sports—Maine’s coast has something for everyone. Quaint seaside villages and towns line the shore as U.S. 1 winds its way toward the easternmost swath of land in the United States at Quoddy Head State Park. Galleries and funky old shops are a major draw, so keep an eye out for roadside retailers crammed with gems. New England’s only national park, Acadia, is a highlight of the tour, drawing more than 4 million visitors per year.
Fly in: Portland International Jetport (PWM), Portland, Maine
Fly out: Portland International Jetport (PWM), Portland, Maine
Day 1: Portland to Brunswick
Use Maine’s maritime capital as your jumping-off point to head farther up the Maine Coast, or, as Mainers call it, “Down East.” Plan to spend half of your first day in Portland, then head to Brunswick for the night.
Portland shows off its restored waterfront at the Old Port. From there, before you depart, you can grab a bite at either of two classic Maine eateries: Gilbert’s Chowder House or Becky’s Diner, or check out what’s new in this city’s buzzy restaurant scene. For a peek at the freshest catch of the day, wander over to the Harbor Fish Market, a Portland institution since 1968, and gaze upon Maine lobsters and other delectable seafood. Two lighthouses on nearby Cape Elizabeth, Two Lights and Portland Head, still stand vigil.
Following U.S. 1, travel northeast along the ragged, island-strewn coast of Down East Maine and make your first stop at the retail outlets of Freeport, home of L.L. Bean. About 3 million people visit the massive flagship store every year, where you can find everything from outerwear to camping equipment. Just 10 miles north of Freeport on U.S. 1, Brunswick is home to the campus of Bowdoin College, the superb Bowdoin College Museum of Art, and also features a superb coastline for kayaking. Plan for dinner and an overnight in Bath.
Logistics: 30 miles; via U.S. 1 N; 30 minutes from Portland airport.
Day 2: Bath
In Bath, Maine’s shipbuilding capital, tour the Maine Maritime Museum, stopping for lunch on the waterfront. Check out the boutiques and antiques shops, or take in the plenitude of beautiful homes. From here it’s a 30-minute detour down Route 127 to Georgetown Island and Reid State Park, where you will find a quiet beach lining Sheepscot Bay—and maybe even a sand dollar or two to take home, if you arrive at low tide. For a stunning vista, make your way to Griffith Head.
Drive north and reconnect with U.S. 1. Continue through the towns of Wiscasset and Damariscotta, where you may find yourself pulling over to stop at the outdoor flea markets and intriguing antiques shops that line the road. Another hour from here is Rockland, where you’ll spend your second night.
Logistics: 52 miles; via U.S. 1 N; 1 hour 15 minutes, starting in Brunswick.
Day 3: Rockland, Camden, and Castine
From Rockland, spend the day cruising on a majestic schooner or reserve a tee time at Samoset Resort’s championship golf course, which overlooks the Rockland Harbor. If you’re an art lover, save some time for Rockland’s Farnsworth Art Museum, the Wyeth Center, and the Center for Maine Contemporary Art.
In Camden and Castine, exquisite inns occupy homes built from inland Maine’s gold and timber. Camden is an ideal place to stay overnight as you make your way closer to Acadia National Park; it is a beautiful seaside town with hundreds of boats bobbing in the harbor, immaculately kept antique homes, streets lined with interesting stores, and restaurants serving sophisticated fare at every turn. The modest hills (by Maine standards, anyway) of nearby Mt. Battie offer good hiking and a great spot from which to picnic and view the surrounding area. It is also one of the hubs for the beloved and historic windjammer fleet—there is no better way to see the area than from the deck of one of these graceful beauties.
Logistics: 62 miles; via U.S. 1 N and Rte. 166 S; 1½ hours, starting in Rockland.
Days 4 and 5: Mount Desert Island and Acadia National Park
On Day 4, head out early for Bar Harbor and plan to spend two nights here, using the bustling village as a jumping-off point for the park—Bar Harbor is less than 5 miles from the entrance to Mount Desert Island’s 27-mile Park Loop Road. Spend at least a day exploring Acadia National Park, New England’s only national park and one of its most popular tourist destinations. Enjoy the island’s natural beauty by kayaking its coast, biking the 45-mile, historic, unpaved, carriage-road system, and driving (by advance reservation only) to the summit of Cadillac Mountain for a stunning panorama.
Logistics: 52 miles; via Rte. 166 N, U.S. 1 N and Rte. 3 E; 1¼ hours, starting in Castine.
Day 6: Bar Harbor to Quoddy Head State Park
About 100 miles farther along U.S. 1 and “Way Down East” is Quoddy Head State Park in Lubec, Maine. Here, on the easternmost tip of land in the United States, sits the West Quoddy Head Light, one of 60 lighthouses that dot Maine’s rugged coastline. Depending on the time of year (and your willingness to get up very early), you may be lucky enough to catch the East Coast’s first sunrise here.
Logistics: 103 miles; via U.S. 1 N; 2½ hours, starting in Bar Harbor. From the park, it’s 3 hours to back to Portland International Jetport.
Connecticut Wineries and Rhode Island Mansions, 5 Days
Travel through the Lower Connecticut River Valley as you meander toward the eastern section of the state’s Wine Trail. While you sample varietals from the area’s best wineries, get a taste of New England’s literary and maritime history along the way. Stay overnight in seaside Mystic, another highlight, and then finish your tour by gawking at Newport’s grand mansions and strolling the gorgeous Cliff Walk.
Fly in: Bradley International Airport (BDL), Hartford
Fly out: T. F. Green Airport (PVD), Warwick
Day 1: Hartford
Start your journey in Hartford, Connecticut. The Mark Twain House and Museum, which Samuel Clemens and his wife built in the city’s Victorian neighborhood of Nook Farm, is adjacent to the Harriet Beecher Stowe Center, which is also worth a visit. Downtown, you can visit the Nutmeg State’s ornate State Capitol and the Wadsworth Atheneum Museum of Art, which houses fine Impressionist and Hudson River School paintings. Sports fans, take note: the Naismith Memorial Basketball Hall of Fame is only a quick detour up Interstate 91, in Springfield, Massachusetts, where Dr. James Naismith invented basketball in 1891. Spend your first night in Hartford.
Day 2: Connecticut River Valley and Southeastern Shore
Just a half-hour southeast of Hartford along Route 2 is your first wine stop, Priam Vineyards, in Colchester. Sample any of the boutique wines before bearing south on Route 149 to explore the centuries-old river towns of East Haddam, Chester, and Essex. In East Haddam, stop at Gillette Castle State Park—with its medieval-style stone mansion built for actor William Gillette—before crossing the Connecticut River on the historic (since 1769), eight-car Hadlyme-Chester ferry (April–November). In Essex, take a ride on the Essex Steam Train—the 12-mile excursion showcases the area’s well-preserved countryside. (You can also return to Essex via riverboat.)
Continue on to Mystic, where the days of wooden ships and whaling adventures live on at Mystic Seaport. This world-class museum offers a peek into the past with restored vessels, historic buildings, figureheads, ship carvings, and much more. Spend your second night in Mystic.
Logistics: 60 miles; via Rte. 2 E; 1 hour, starting in Hartford (not including stops).
Day 3: Connecticut Wine Trail
A patchwork of six wineries—the heart of the eastern section of the Connecticut Wine Trail —sits in the southeastern corner of the state. Taste through the portfolio at each of the picturesque vineyards until you find the perfect bottle to take home; many wineries offer self-guided walks through peaceful vineyards, allowing you to roam on your own. Stonington Vineyards has daily guided tours, and Jonathan Edwards Winery, farther inland in North Stonington, is a serene setting for picnics. Cap off the day by crossing the state line into Rhode Island and spend the night in Watch Hill. You can wander the grounds of the Watch Hill Lighthouse; in its museum, open midweek afternoons in summer, you can see the original Fresnel lens, a binnacle, mariners’ sea chests, and historical documents and photos about the lighthouse and the area.
Logistics: 13½ miles; via U.S. 1 N; 25 minutes, starting in Mystic (not including stops).
Days 4 and 5: Rhode Island’s Beaches and Newport’s Mansions
En route to Newport along U.S. 1 from Watch Hill, sandy beaches dot the coast from Misquamicut and Weekapaug to Charlestown and Narragansett. If it’s summer and the weather is fine, spend the afternoon at the beach before continuing on to Newport. Despite its Colonial downtown and seaside parks, to most people Newport means mansions—the most opulent enclave of private homes ever built in the United States. Turn-of-the-20th-century “summer cottages” such as the Breakers and Marble House are must-sees. Embark on the scenic Cliff Walk for remarkable views of these great houses on one side and the Atlantic Ocean on the other. Newport’s downtown is excellent for window-shopping, and there are plenty of places to enjoy fresh seafood.
Newport is known to many as the sailing capital of the East Coast, and you may get the best feel for it from the deck of a schooner cruising its famous harbor. Tours generally last around 90 minutes, and some offer beverages and snacks. Tennis enthusiasts can visit the International Tennis Hall of Fame, which, along with exhibits focusing on the legends of the game, has a unique interior designed by architect Stanford White. You can easily spend a few days exploring Newport.
Logistics: 39½ miles; via U.S. 1 N; 1 hour, starting in Watch Hill. From Newport, it is 26 miles (30 minutes) to T. F. Green Airport via Rte. 138 W and Rte. 4 N.
Best of Vermont, 7 Days
Following roads that weave through the Green Mountains and charming towns, this 200-mile journey is ideal at any time of year and covers Vermont from the bottom of the state to the top.
Fly in: Bradley International Airport (BDL), Hartford
Fly out: Burlington International Airport (BTV), Burlington
Day 1: Brattleboro
Artsy Brattleboro is the perfect place to begin a tour of Vermont, and it’s worth taking a day to do some shopping and exploring. Catch a movie at the art deco Latchis Theatre, browse in a bookstore, or simply grab a cup of joe and people-watch. For dinner, make a reservation well in advance at tiny T.J. Buckley’s, one of the best restaurants in the region. Spend your first night in Brattleboro.
Logistics: 78 miles; via I–91 N; 1 hour and 15 minutes from Bradley airport.
Days 2-4: Killington
Depart Brattleboro heading west on Route 9 and link up with Route 100 in Wilmington. As you travel north along the eastern edge of Green Mountain National Forest, you’ll pass a plethora of panoramic overlooks and delightful ski towns. Stop to snap a photo, or take a moment to peruse the selection at a funky general store, as you make your way toward gigantic Killington Peak. Spend the next three nights in Killington, the largest ski resort in Vermont, and an outdoor playground year-round. A tip for skiers: one of the closest places to the slopes to stay is The Mountain Top Inn & Resort.
Wake up early to carve the mountain’s fresh powder in winter. Nonskiers can still enjoy the snow, whether at the tubing park, on a snowmobile adventure, or in snowshoes on one of several trails. In summer, long after the ground has thawed, those trails are opened to mountain bikers and hikers. For a more leisurely activity, try your hand at the 18-hole disc-golf course. The excellent Grand Spa is also a lovely way to spend the day.
Logistics: 94 miles; via Rte. 9 W, Rte. 100 N, 2½ hours, starting in Brattleboro.
Day 5: Killington to Burlington
Continue on Route 100 north until you reach Hancock, then head west on Route 125. Welcome to the land of poet Robert Frost, who spent almost 40 years living in Vermont, summering in the nearby tiny mountain town of Ripton, where he wrote numerous poems. Plaques along the 1.2-mile Robert Frost Interpretive Trail, a quiet woodland walk that takes about 30 minutes, display commemorative quotes from his poems, including his classic, “The Road Not Taken.” After your stroll, head north on U.S. 7 until you hit Burlington.
Burlington, Vermont’s largest city and home to the University of Vermont, is located on the eastern shore of acadia. Bustling in the summer and fall, the Burlington Farmers Market is filled with everything from organic meats and cheeses to freshly cut flowers and maple syrup. Spend the night in Burlington. In the evening, check out Nectar’s, where the band Phish played their first bar gig, or wander into any of the many other pubs and cafés that attract local musicians.
Logistics: 84 miles; via Rte. 100 N, Rte. 125 W, and U.S. 7 N; 2½ hours, starting in Killington.
Day 6: Shelburne and Lake Champlain
On your second day in Burlington, you can take a day trip south to Shelburne and family-friendly Shelburne Farms. Watch the process of making cheese from start to finish, or wander the gorgeous 1,400-acre estate designed by Frederick Law Olmsted, co-designer of New York’s Central Park. The grounds overlook beautiful Lake Champlain and make the perfect setting for a picnic. In winter Shelburne Farms offers sleigh rides and other themed activities.
Logistics: 6.5 miles via U.S. 7 to Shelburne Farms; 30 minutes round-trip.
Day 7: Stowe
A 30-minute drive down Interstate 89 from Burlington reunites you with Route 100 in the town of Waterbury. Head north in the direction of Stowe, and in under 2 miles you can make the obligatory pit stop at Ben & Jerry’s Ice Cream Factory. The factory tour offers a lively behind-the-scenes look at how their ice cream is made; at the end of the tour, you get to taste limited-release creations only available at the factory before voting on your favorites.
Next, set out for the village of Stowe. Its proximity to Mt. Mansfield (Vermont’s highest peak at 4,395 feet) has made Stowe a popular ski destination since the 1930s. If there’s snow on the ground, hit the slopes, hitch a ride on a one-horse open sleigh, or simply put your feet up by the fire and enjoy a Heady Topper (an unfiltered, hoppy, American Double IPA beloved by beer aficionados the world over). In warmer weather, pop into the cute shops and art galleries that line the town’s main street and sample some of the finest cheddar cheese and maple syrup that Vermont has to offer. Rejuvenate yourself at Topnotch Resort, which offers more than 100 different treatments. Spend your final night here.
Logistics: 36 miles; via I–89 S and Rte. 100 N; 45 minutes, starting in Burlington. From Stowe to the Burlington airport: 33 miles; via Rte. 100 and I–89 N; 41 minutes.