The Mighty American Road Trip: Cruise Through the Sweeping Mountain Ranges and Colonial Cities of New England

2. Get on the water and take a sailing lesson (Newport, RI)

Sailing is such an integral part of the culture in Newport, RI, (as well as many of the coastal Northeastern towns), the two have become practically synonymous. You can charter a sailboat (or even a yacht, if that’s the kind of budget you’re working with) through many operators in the Newport area, but for those looking to learn the ropes, take a five-hour introductory lesson with Newport Sailing School and Tours. And if you want to look the part, don a Vineyard Vines fleece vest—it can get chilly out there on the harbor, after all—and throw on a pair of Sperry leather boat shoes. Or don’t—a plain old sweatshirt is fine by us.

A day spent sailing on Newport Harbor or Narragansett Bay wouldn’t be complete without a classic New England-style lobster roll. Check out the Newport Lobster Shack, which only serves up fresh and local catches, or the waterfront Easton’s Beach Snack Bar for some of the best.

3. Watch the world’s largest regatta before checking out Harvard Square (Cambridge, MA)

You already know that you’re deep in the heart of Ivy League country, so why not check out an athletic event featuring the quintessentially prep-school sport of rowing?

The Head of the Charles regatta, which takes place every year during one of the last weekends in October, isn’t just the world’s largest two-day rowing event, it’s a great place to grab a few beers and enjoy the crisp fall weather. We recommend grabbing a spot on one of the river’s many bridges—not only will you have snagged one of the best seats in the house, there’s a good chance you’ll see more than a few boats collide on the notoriously difficult (and often crowded) race course. 

After a few hours of spectating—or if you’re not in town on Head of the Charles weekend—take the short walk over to Harvard Square, where you can grab a bite at Beat Brasserie, Alden & Harlow, or the appropriately themed Boathouse pub on Mt. Auburn St.

4. No plane, no parachute—jump into indoor skydiving (Nashua, NH)

You don’t need to jump out of a plane or worry about your parachute failing to open to get your adrenaline pumping at SkyVenture New Hampshire, where you can also surf and rock climb indoors. If you’re more interested in getting outside, however, check out Mine Falls Park, a riverfront Nashua fixture that offers serene trails for hiking and mountain biking, as well as opportunities for boating and fishing. 

Back in town, check out Fody’s Great American Tavern, a lively saloon serving up pub grub and cocktails, or The Peddler’s Daughter, located right off Main Street on the river.

5. Ski Mount Snow in the winter, golf nearby in the summer (West Dover, VT)

Your first adventure in Vermont will take you to Wilmington, a small historic town on the southern edge of the state. While the city’s 18th- and 19th-Century architecture is guaranteed to charm, the real reason to spend a night here, says Ping, is to visit Mount Snow in nearby West Dover.

A top-notch ski resort during the winter months, Mount Snow also offers mountain biking excursions and relaxing rounds of golf in the summer. After a day outdoors, Ping recommends stopping by Wahoo’s Eatery for a burger made from Vermont grass-fed beef.

6. Sample tangy cheddar at the second-oldest cheese factory in the U.S. (Plymouth, VT)

Like many cities and towns throughout New England, Plymouth is packed with presidential history.

Not only did President Calvin Coolidge grow up here—history buffs will want to make a visit to the Coolidge Homestead, the 30th president’s childhood home—his father, Col. John Coolidge, helped co-found the Plymouth Cheese Factory back in 1890. Today, artisan cheesemaker Jesse Werner continues to produce American heritage cheeses from local raw cow’s milk in the original building, constructed in the late 19th Century. 

On your way out of Plymouth, make a pit stop at the Killington Resort for a jaw-dropping view of the Green Mountains from the K1-Express Gondola, the highest lift in Vermont, according to Ping.  

7. Snap a pic of Vermont’s most photogenic waterfall—Moss Glen Falls (Granville, VT)

Just off the west side of Vermont’s Route 100 lies one of the state’s most beautiful and easy-to-access destinations: Moss Glen Falls, just three miles north of the village of Granville. Apparently, the small pounds around Granville Gulf also happen to be one of the best places to spot a wild moose. (To improve your odds of catching a glimpse of one, Ping recommends making a visit at dawn or dusk.)

After capturing an epic shot of Moss Glen Falls (or maybe a moose)—and we get it, you’re gonna #nofilter that Instagram post—make the 15-minute drive into the town of Warren. Here, you can dive right into swimming or kayaking the Mad River Valley. If the weather is nice, take a dip in one of the area’s granite swimming holes. For some delicious farm-to-table fare, Ping suggests making a visit to nearby restaurant Peasant, which also serves up a wide selection of beer, wine, and cocktails. 

8. End your trip on a high note with some world-class hiking and mountain biking (Stowe, VT)

Make the picture-perfect town of Stowe your home base for exploring Mount Mansfield, which happens to be the highest peak in Vermont at 4,393 feet above sea level. 

Hiking, biking, golfing, skiing—the options are pretty much endless on Mount Mansfield. During the summer months, hike the Mount Mansfield Loop Trail, a fairly difficult eight-mile hike that’ll reward you with stunning mountain views and lush flora and fauna. In the winter, go skiing or snowboarding at the Stowe Mountain Resort. 

After a day on the mountain, grab a tasting at the Trapp Family Brewery (yes, it’s owned by the actual von Trapp family from The Sound of Music) or splurge on a sumptuous dish like lobster with bourbon-tarragon sauce at The Bistro at Ten Acres to celebrate the end of your trip.