Best New England Late Summer Adventures

This article originally appeared in the August 2017 digital issue of Yankee and may have been updated for this special collection.

In New England, each season has an unwritten expiration date, and summer’s sneaks up fastest of all. It’s critical to heed the warning signs—a sudden, sharp chill in the morning air, a scattering of early-defector leaves on the ground—because some of New England’s best experiences will have to wait until next summer unless you get moving. If you’re determined not to surrender summer without a “last hurrah” adventure or two, here are 10 ways to make the most of the season’s remaining days.

Sleep on a Houseboat in Riggs CoveGeorgetown, Maine

Maybe you’ve dreamed of owning a boat but were put off by, you know, the ownership part. There’s a blissfully hassle-free alternative: Through October, book a three-night stay or longer aboard one of Riggs Cove Rentals’ three houseboats, and, moored in the midst of one of Maine’s prettiest coves, you’ll find the relaxation you deserve.

The friendly dockhands at the Derecktor Robinhood marina will ferry you and any groceries and gear out to your floating cottage and show you how everything works. Ideal for two grown-ups or a family of four, each boat has a fully equipped galley kitchen, barbecue grill, head with a sink and hot shower, and a DVD player. You’ll also have a motorized skiff and two kayaks for exploring the cove’s crannies, spying on seals, and checking out shipwrecks and oyster farms. Or head to shore for wicked good coffee and fresh pastries at the Robinhood Free Meetinghouse; free Wi-Fi in the library, one of four vintage buildings in the marina’s miniature seaport village; or a meal and some camaraderie at the dockside Osprey restaurant. If you’re an experienced sailor, an 18-foot Cape Dory is available free for your use, too.

Of course, you may be content to simply stay “home.” The sun rises early along the Maine coast and so should you, to sit on your deck and sip coffee while morning mist lingers and seagulls swoop. Wave to lobstermen as they head out to tend traps, and make a mental note to try to flag them down as they return with the day’s catch: Lobster straight from the cove to your cooking pot is an unforgettable treat that practically guarantees sweet dreams, as the gentle rock-a-bye motion of the water lulls you to sleep. robinhoodmarinecenter.com/riggs-cove-rentals

See a Broadway-Caliber Show at the Weston PlayhouseWeston, Vermont

It’s the 81st and final season of summer-only theater in this storybook Vermont town famous for its playhouse with 300 seats—enough for more than half its resident population. But this is not a tragic ending for the Weston Playhouse, the state’s oldest professional theater. This fall, after more than a decade of planning and fundraising, Weston will become a year-round destination for theater fans with the opening of a new, equipped-for-the-future community arts center designed to harmonize with its rural setting at Walker Farm.

The original theater, situated in a rebuilt Greek Revival church on the town green, will still host summer performances each year. But you should hurry and get there this season, because the excitement surrounding this nonprofit Equity company’s expansion is palpable. An immersive evening of theater begins with show-themed drinks and dinner at the playhouse’s own waterfall-view restaurant, after which you’ll take your seat for the performance, which has set you back a fraction of what it costs to see a Broadway show these days. (Tickets for late-summer mainstage productions of The Music Man and Long Day’s Journey Into Night start at $15.)

After the curtain call, the action continues in the downstairs cabaret, as the actors you’ve just seen onstage join Young Company players for an hour of music and comedic sketches. You’ll drive away wondering if you’ve ever spent six summer hours more entertained. westonplayhouse.org

Giddy-up to a Rodeo at Pond Hill RanchCastleton, Vermont

Somewhere along the dirt road that leads to the 2,000-plus-acre Pond Hill Ranch—the largest working ranch east of the Mississippi—New England ends, and the West begins. Horse buying, selling, leasing, and boarding, and pony and trail rides are the focus of this fourth-generation-run equine business. But for 47 years, it’s the honest-to-goodness rodeos here that have attracted pro circuit cowboys, cowgirls, and sports fans.

Kicking off at 8 p.m. every Saturday from July through Labor Day weekend, the rodeo is alcohol-free and family-oriented, but it’s no clown-filled county fair show. Serious prize money is at stake, and from the moment the first bucking bronc bursts out of the chute, you’ll see all the amazing rodeo skills that have evolved from cowboys working cattle. From team roping to steer wrestling to barrel racing, the announcer helps rodeo newbies understand each event’s requirements, which—like the humane treatment of animals—are dictated by a professional rodeo governing body.

As the setting sun bathes the Adirondacks in golden light, the view westward from your bleacher seat alone is worth the price of admission: $12 for adults, $6 for kids 6 to 12. And when it’s time for novices to attempt to ride one of the ranch’s own 1,500-pound bucking bulls for a qualifying eight seconds, you’ll appreciate how long every lingering moment of summer can seem if you try something new. pondhillranch.com

Boogie Board at Hampton BeachHampton Beach, New Hampshire

Don’t let summer slip away without feeling the tingle of saltwater on your skin. Wading in up to your ankles doesn’t count—we’re talking about giving yourself over to the surge of the ocean and letting it carry you along on an exhilarating ride. And for our money, the best place to do it is New England’s boogie boarding capital, Hampton Beach, a destination known for its consistent surf and vigilant lifeguards.

By August, the water is as warm as it’ll be all year along this stretch of shore, which was ranked the third best beach in the country for water quality by the National Resources Defense Council. And kids aren’t the only ones flutter-kicking out to meet incoming waves: This affordable, easy-to-learn water sport is fun for anyone with basic swimming skills. Colorful foam boogie boards are sold at boardwalk shops, or you can rent a board for the day at Cinnamon Rainbows Surf Co., three miles north on Ocean Boulevard.

After getting thoroughly waterlogged, take advantage of the fact that you’re just steps away from nostalgic arcade games, mini golf, nightly free concerts at the Sea Shell Stage, ticketed performances at the Hampton Beach Casino Ballroom, and every tasty beach treat imaginable. Mondays are movie night on the beach, and the Wednesday fireworks displays continue through August. But once the annual Hampton Beach Seafood Festival, held the weekend after Labor Day, is a wrap, the sand has run out of the summer-season hourglass. hamptonbeach.org

Star-Gaze at the AMC Highland CenterBretton Woods, New Hampshire

With no cities or even small towns nearby, the sky above the Highland Center at Crawford Notch is inky black and sparkling with stars on clear, late summer nights. But you don’t have to wait for the sun to go down to take advantage of the giant, high-powered Celestron telescope positioned on the lodge’s front lawn: Free stargazing activities for both overnight guests and the public are offered nightly and daily through late August thanks to an innovative collaboration with Carthage Institute of Astronomy director and AMC member Douglas Arion.

By day, undergraduate interns from several colleges aim the telescope at the sun, engaging visitors in an examination of the explosive surface of our closest star. By night, interns, staff, and guest speakers lead all-ages programs that dig deeper into such topics as the formation of the solar system and “dark sky” preservation. On occasions when clouds obscure the constellations, the Highland Center even has an indoor planetarium, so you’re guaranteed a starry night.

Programs are open to walk-in participants, although you’ll want to call ahead (603-278-4453) if you’d like to attend the August 12 Perseid meteor shower viewing party, when dinner may be reserved for a fee, or the solar eclipse viewing party on August 21. (Although New Hampshire will experience only a partial eclipse, Arion will be on location in the western U.S. to share the total eclipse with participants.)

And if you happen to spot a shooting star during your visit, go ahead and make a wish: Standing in this natural amphitheater at the edge of the Pemigewasset Wilderness in the midst of the skyscraping White Mountains, you may find nature’s power impossible to doubt. outdoors.org/astronomy

Pick Peaches at Nashoba Valley WineryBolton, Massachusetts

Apples are not quite ready yet; berries are on the decline. But as August days trickle away, peaches are in their prime—and to experience New England’s ultimate place to take a bite of this juicy, late-summer crop, pay a visit to Nashoba Valley Winery, just a 35-minute drive from Boston. The winery cultivates a dozen varieties of peaches for use in its after-dinner wine, brandy, and desserts at J’s Restaurant, and it’s a bit of a well-kept secret that they’re also yours for the picking, priced by the peck or half-peck bag.

For a truly memorable visit, start by going to the winery’s website and reserving one of the limited number of gourmet picnic lunches that are offered every day except Mondays and Tuesdays. The orchard itself opens at 11 a.m., and you’ll walk about 80 yards from the parking lot to the trees laden with velvet-skinned fruit. If peach picking is an unfamiliar enterprise, look for the helpful employees patrolling the grounds on Segways, who can show you how to select peaches that are just shy of ripe. They’ll guide you to varieties that suit your palate, too, be they delicate, flowery-favored white peaches or super-sweet, doughnut-shaped Saturn peaches.

Savor your picnic on the winery’s vine-shaded porch, then venture inside to taste Nashoba Valley’s diverse wines. It’s uncanny how winemaker Nathan Gilman’s peach dessert wine captures the juiciness of biting into a fresh peach. Stash away a bottle for later this winter, and summer memories will be a cork pop away.nashobawinery.com

Take In a Concert at TanglewoodLenox, Massachusetts

Right up until rocker Melissa Etheridge hits the last note of her encore on September 3, you haven’t missed your chance to hear a performance at New England’s most famous fresh-air concert venue. At 80 years old, Tanglewood is as spry as ever, with a summer lineup to enrapture fans of diverse music genres: classical, contemporary, chamber, choral, opera, pop, rock, folk, cinematic. And with ample covered seating and lawn tickets for all shows, sold-out performances are rare, so you can almost always make a spur-of-the-moment decision to pack a picnic and go.

In the span of five days in August, you can watch E.T. on big screens as conductor Keith Lockhart and the Boston Pops perform John Williams’s Academy Award–winning score; spend an hour doing yoga with an instructor from Kripalu as the Boston Symphony Orchestra rehearses; allow the familiar melodies of Beethoven’s Symphony No. 9 to stir your emotions; and sing along with one of the most distinctive voices of a generation, Sting.

Moments at Tanglewood have a way of claiming a permanent place in your memory. And that’s the optimal use of waning summer days, particularly if you can introduce the magic of live music to a child. For all except popular artist concerts, Tanglewood lawn seats are free for up to four kids under the age of 18 accompanied by a parent. Plus, the gates open at noon for activity-filled Summer Sundays, so families can spend preconcert hours enjoying games, local-food tastings, face painting, and interactive experiences; attending lectures, performances, and musical demonstrations; and exploring Tanglewood’s picturesque gardens and grounds. tanglewood.org

Get Lost in Lyman Orchards’ Sunflower MazeMiddlefield, Connecticut

There’s one place in New England where it’s impossible to be despondent about summer’s impending good-bye: the sunflower maze. Imagine wandering earthy pathways through a field of 350,000 ornamental sunflowers—dazzling yellow, with a few deep orange and red blooms for striking contrast. It’s a labyrinth of happiness. A cheerful escape. And since these sunflowers are pollen-free, even allergy sufferers smile.

Open for only about four weeks from late July through late August, the bird-and-butterfly-filled sunflower maze at Lyman Orchards is more than an agricultural adventure and a colorful photo op. It’s also a chance to jump-start kids’ brains before school resumes, since themed trivia challenges help them decide which way to turn at the crossroads and forks within the maze (whose design this year was inspired by the underwater world of the PBS Kids series Splash and Bubbles).

On weekends, you can start off your visit with farm-fresh breakfast fare at the orchard’s Apple Barrel market. And there’s plenty more to do once you’ve navigated the sea of sunflowers: Shop for produce, pies, and other baked goods. Pick your own peaches and, by mid-August, pears and early apples. Golf nine or 18 holes, or practice your swing at the driving range. Indeed, diversification has helped make this 276-year-old farm one of the oldest family-owned businesses in the nation.

There’s one more feel-good reason to go. Lyman Orchards donates $1 from each sunflower maze ticket sold to the Connecticut Children’s Medical Center pediatric cancer unit. So, your time in the sun has lasting positive effects. lymanorchards.com

Catch a Drive-In Movie by the Sea in WesterlyWesterly, Rhode Island

Remember the time before on-demand movies, when anticipating the arrival of summer blockbusters was half the fun? There’s an oceanview parking lot across the street from Wuskenau Town Beach on Winnapaug Pond where you can relive the giddy excitement of summer nights at the drive-in for the retro price of $12 per carload.

Screenings start at 9 p.m. on Thursdays and Fridays through August, and 8 p.m. Fridays through mid-October. But the buildup to classic flicks such as Back to the Future, Planet of the Apes, and Grease begins when gates open at 6:30 p.m. There’s room for about 100 cars in the main lot, but you’ll want to park early for the best sight lines and sound. Toting chairs from the overflow lot is an option, too, and you can tune in the audio on 96.3 FM for optimal volume.

The concession stand’s hot dogs, candy, popcorn, and Coca-Cola in glass bottles are all you need to complete a nostalgic evening. But you’re in the Ocean State, so don’t just camp out until sundown. Walk along the sandy shore. Pick up clam fritters and hot or cold lobster rolls from Two Little Fish or the Windjammer Surf Bar, both of which are steps away from the big screen.

Just remember to get back an hour before show time, so you don’t miss the preview reel’s entertaining hodgepodge of old-school movie countdowns, TV commercials from the ’70s, and local advertisements. It sets the mood for draping an arm around your summer love. Or for watching blanket-wrapped kids’ reactions to scenes you first saw decades ago with your own parents. misquamicut.org

Cheer for the Home Team at a PawSox GamePawtucket, Rhode Island

The sun sinks a bit earlier behind the left-field wall now, and summer’s peak swelter has passed. But play on the field is heating up, as the days remaining for players to make a major league impression dwindle. You can’t beat the last month of the season for an outing to one of the country’s most storied minor league ballparks—especially on a Saturday night, when music-synced post-game fireworks punctuate a win or redeem a loss. And with general admission tickets priced under $10 even during popular promotions such as August 11’s Nomar Garciaparra bobblehead giveaway, there’s no need to balk at the cost.

The PawSox—the Triple-A affiliate of the Boston Red Sox—may be working on a deal for a new stadium, but their current home at the New Deal-era McCoy Stadium is no has-been in its 75th anniversary season. Fans are lining up for new, healthier food options. Hot prospects are getting the coveted call-up to the big leagues. And the “Paws for a Cause” initiative is transforming every home game into an opportunity for a community nonprofit to raise awareness and garner support.

Arrive when the stadium opens (an hour before most games, 90 minutes on Saturdays) to walk the Hallway of History, where exhibits celebrate Hall of Famers who’ve worn PawSox uniforms. There’s also a tribute to McCoy’s most legendary moment—or rather, eight hours and 25 minutes, which was the length of the longest game in professional baseball history, played here in 1981. And don’t forget to bring your fishing supplies: a permanent marker, a rope, and a plastic pail or cut-open milk jug. The dugouts’ design makes “fishing for autographs” a ballpark tradition you won’t find anywhere else. Dangle a baseball, a hat, something quirky—and leave with a summer of ’17 souvenir signed by a rising star. pawsox.com