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A winding road in western Maine is a great place to view fall foliage. (Credit: Visit Maine)

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The sun has unofficially set on summer.

But though we’ll soon be swapping sundresses for sweater dresses and flip-flops for cozy socks, our sense of adventure need not shrink along with the hours of daylight.

Though summer days may be behind us, we’re still closer to the warmer weather of August than the frigid temps of February. 

Fall may bring the added hustle and bustle — the end of slower days at work — but it’s prime time for a quick road trip. Further north on the eastern seaboard, New England transforms into arguably the world’s most colorful region come fall. And it has quaint and modern experiences for oenophiles and beer drinkers, foodies and football fans.

Whether it’s necessary to roll the windows down or turn the heat up for the first time this season, consider New England the quintessential spot for a final road trip in 2019.

Boston, Mass.

The Boston skyline. (Credit: Kyle Klein/Greater Boston Convention & Visitors Bureau)

There will be plenty of time to hit the countryside during this trip, but the adventure begins in a city, albeit one that carries a special sort of charm. Sixteen times smaller than New York City, Boston packs a whole lot of activities. The sports teams are a primary source of pride. The Red Sox and Patriots are the reigning MLB and NFL champions, respectively, and the Bruins went to the Stanley Cup finals this year. The Sox aren’t the favorites to win it all this year — and may not even make the playoffs — but a trip to Fenway Park is worth it if they’re playing. Steeped in history, the 107-year-old ballpark epitomizes the city: small and quirky. With a capacity of just under 38,000 people, it’s the fourth-smallest park in Major League Baseball. Its quirks include the 37.2-foot left-field wall known as the Green Monster, Pesky’s Pole and a lone red seat in section 42 honoring a homer hit by Ted Williams in 1946.

Those who prefer spirits to sports will want to cozy up to the bartender at Backbar. Part of the fun is finding it — its door is inconspicuously unmarked. Inside, the drinks are as creative as the street art that covers the walls. Think cocktails infused with lavender and a bartender not afraid to play with fire. Pro tip: If possible, try going on a weeknight. Despite the nondescript door, this place isn’t a secret — weekends are crowded.

Though the famed university is technically in Cambridge, the Harvard football team plays across the bridge in Boston. Built in 1903, the stadium was designated a National Historic Landmark in 1987. It’s worth heading across the bridge to Harvard Square — the area is alive with bars, restaurants and independent coffee and bookshops. On campus, Harvard Square, complete with centuries-old architecture, is an ideal spot to plop down and read a book or have a picnic on a mild afternoon. Those feeling particularly touristy can head to the Cheers Restaurant on Beacon Street, a 20-minute ride away on the Red Line.

Though one may want to save their cliche activity for Boston Commons, particularly those fond of history. The 50-acre Common is the oldest park in the U.S., dating from 1634, and is the burial spot of Boston Tea Party participant and Revolutionary War soldier Samuel Sprague.

New Hampshire

New Hampshire in autumn.

The trip will take a turn to focus on the scenery over the scene as travelers head to New Hampshire. Though the state’s motto is in-your-face — “live free or die” — New Hampshire, like Vermont and Maine to follow, is anything but unpretentious. Travelers can work off the cocktails and hotdogs consumed in Boston on Mt. Washington, the highest peak in the northeastern U.S. On clear days, hikers can see up to 130 miles into the distance, and moose sightings are possible. Those not in the mood to climb all 6,288 feet can take the auto road and get their cars the obligatory “This Car Climbed Mount Washington” bumper sticker. It’s a badge of honor in the northeast.

Rehydrate the next day with a craft beer or three. Woodstock Inn Brewery, named for its town, is home to Old Man Oatmeal Stout, dark, creamy brew with notes of coffee and chocolate. It has a velvety head and mouthfeel and counts as a full meal. Guests who get too hoppy can spend the night in one of the 40 cozy rooms and suites, many of which include gas fireplaces ideal for ushering in nippy nights. In New London, Flying Goose Brew Pub gets high marks for its easygoing atmosphere, mountain views and ever-changing Flying Goose Pale Ale, which gets a new iteration with each batch.


Fall foliage in Vermont.

Craft beer enthusiasts often call Vermont paradise. On Sept. 28, people who enjoy running for beer can partake in the Vermont Craft Beer Half Marathon, which starts in downtown St. Albans and goes through the rolling terrain of the Missisquoi Valley Rail Trail. It goes without saying there’s craft beer at the finish line. Those who prefer to drink without leg cramps have plenty of options to choose from. Hill Farmstead Brewery was named best brewery in the world for 2018, its fifth win in a row and sixth in the last seven years. Located in Greensboro Bend, it’s not exactly in the middle of a major hub, but it doesn’t stop the true craft beer enthusiast from making the trip. One sip of the Arthur, crafted from American malted barley, American European hops and the brewery’s distinctive farmhouse yeast, and visitors will understand why.

Long Trail Brewing Company in Bridgewater Corners offers brews, food and a riverfront view accented by foliage come fall. Long Trail Ale, which is toasting to its 30th anniversary in 2019, is a full-bodied amber ale with a clean, complex flavor. In Shelbourne, Fiddlehead Brewing Company’s tasting room may be small, but the beer is something to write home about. The Hodad is a porter brewed with toasted coconut flakes, cacao nibs, vanilla bean and lactose. The Hefeweizen is lighter, boasting notes of banana esters and a subtle clove character. For more elbowroom, take a few favorite brews next-door, were Folino’s Pizzamakes brick-oven pies and is BYOB.

One of the pioneers on the craft scene, the Alchemist, located in Stowe, is home to a cult favorite: The Heady Topper. The IPA with citrus flavors often sells out of cans. The large outdoor area has lawn games and views for days of the mountains. Consider staying a while in Stowe. Come winter, the mountains are made for skiing, but in the fall they’re perfect for leaf-peeping and exploring by foot.

The recreation path begins in town and heads to the mountains. It’s beginner and bike-friendly and offers something picturesque, from foliage to water, at every turn. For another experience worthy of an Instagram (but worth putting your phone down for and just enjoying), Moss Glen Falls is surrounded by trees and rolls through a ravine.

Portland, Maine

Lobster on the wharf at Portland Lobster Company. (Credit:

About an eight-hour drive from New York, Maine is worth the trek if only for a late-season lobster roll. The Portland Lobster Company does ’em right. Made with fresh meat that boasts a touch of sweetness, it’s served on a toasted roll. No need to choose between mayo or lemon — both come on the side. Diners can also go out on a limb and try a clam, scallop or crabmeat roll. Rest tired legs and settle stomachs at The Westin. Once recovered from a lobster (or clam) roll, head to the rooftop, home of Top of the East. Floor-to-ceiling windows allow guests to take in 360-degree views of the city. Though the ambiance is chic and modern, the menu is as approachable as the staff. Think bacon and grilled cheese sandwiches, flatbreads, lobster sliders (obviously) and warm cookies for dessert.

Though New England is often best known for its beer and seafood, oenophiles will feel at home at MJ’s Wine Bar. The airy, cozy space is a detour from the farmhouse-style spots on this itinerary. There’s plenty of lighting, clean white walls and wine from everywhere from France to Hungary. It’s unpretentious, with more of a coffee shop vibe. The clientele tends to be families, young professionals and art students.

Those who have seen enough foliage by now can seek out lighthouses. Portland Head Light, found on Cape Elizabeth, Maine, marks the entrance to the primary shopping channel into Portland Harbor.

About an hour north of Portland, Maine’s Botanical Gardens are still in bloom in autumn. Open until Oct. 31, guests can take guided tours at 11 a.m. Reservations are not required, and it’s highly recommended for those who don’t know a Dahlia from a Hydrangea (the latter of which can be seen into October).