The distance between Max Yasgur's former farm in Bethel, New York, to a NASCAR track in Watkins Glen is 155 miles. It's also 50 years and the difference between two generations—one with 400,000 muddy-faced hippies crammed under tarps chanting "no rain!" while waiting for Santana to hit the stage, the other using smartphones to determine whether to see Miley Cyrus, Chance the Rapper, or Leon Bridges. A road trip between the original 1969 Woodstock site and the Woodstock 50 festival being held this August takes roughly two hours and 45 minutes if you drive straight through. But this stretch of highway is jammed with wineries, nature preserves, bed-and-breakfasts, Spiedie sandwiches, and all the '60s rock nostalgia you could ever want, so turn it into a real three-day drive from New York City.
Day 1: Bethel Woods Center for the Arts
Start in Bethel, about two hours north of New York City, or roughly an hour west from New York Stewart International Airport in the Hudson Valley. The one-time Borscht Belt stop where comedians from Jackie Mason to Woody Allen played Catskill Mountains hotels changed forever when Yasgur leased his field to Woodstock promoters in 1969. Today, the town of 4,200 regularly celebrates baby-boomer culture; the 13-year-old Bethel Woods Center for the Arts, at the original festival site, is displaying the "We Are Golden" exhibit all summer. Memorabilia includes Joan Baez' Woodstock contract and original chunks of the stage and loudspeakers. Woodstock-anniversary week in August brings Ringo Starr and his All Starr Band, plus Santana and the Doobie Brothers and others, to its amphitheater; before the concerts, pair locally distilled whiskeys with lamb, or gnocchi with wild mushrooms, while taking in local bands at the nearby Dancing Cat Saloon.
Bonafide hippies might ignore the hydromassage waterfalls at the Woodloch Pines Resort spa, but you shouldn't. Drive the 45 minutes from Bethel, across the Pennsylvania state line, to enjoy the 300-acre resort’s nature trails, zip-lines, and world-class golf course.
Day 2: Binghamton
An hour and a half west of Bethel, Binghamton is a college town best known for its historic carousels—the one in Ross Park is 99 years old, with 60 colorful jumping horses and a Wurlitzer organ, plus a surrounding zoo. Binghamton University's Nature Preserve is a contemplative break from the rock 'n' roll you'll be celebrating all week, and its 182 acres include wetland trails, 200 types of birds, and the occasional porcupine.
Up here, they love their sandwiches: Lupo's S&S Char-Pit is the home of the Spiedie, a Philly-cheesesteak-ish sub with pork or chicken and a secret-sauce marinade (the key ingredients are garlic, vinegar, and oregano) that you can bring home in a bottle. There’s no Ritz-Carlton around here, so stay at the Park House Bed & Breakfast, in an 1800s Victorian, which serves cherry pistachio scones and sour-cream coffee cake.
Day 3: Ithaca
This town is mostly famous for Cornell University—check out the I.M. Pei–designed Johnson Museum of Art on campus, with Edward Hopper and Albert Bierstadt paintings in its large collection—but Ithaca is also the start to Finger Lakes country, which is growing in popularity for its Riesling-dominated vineyards overlooking the water and gorges. Six Mile Creek Vineyard, in a restored Dutch colonial barn, distills its own vodka and gin, and also makes peach-and-butterscotch-flavored Chardonnays; the southern tip of long, skinny Cayuga Lake is a placid area for wine cruises and waterfront dining at the steak-and-seafood Boatyard Grill. And if you need time out of the car, Ithaca is also home to 150 waterfalls, plus valleys and gorges you can tour via helicopter.
Day 4: Woodstock 50
The 50th-anniversary concert, created in part by original Woodstock promoter Michael Lang, is at Watkins Glen International, a speedway that doubles as a concert stage for new acts like Chance, Miley, and Courtney Barnett and old hands from David Crosby to Dead and Co. Book rooms right away if you plan to be in town for the festival: The Harbor Hotel, overlooking Seneca Lake, is already sold out on Saturday night. (The Blackberry Inn B&B, in a pink 1830s Greek-revival farmhouse, is an alternative.) On the off chance that you prefer to see actual auto racing at the speedway rather than celebrating the ‘60s yet again, Watkins Glen transforms over Labor Day weekend into a Grand Prix Festival, with car shows, 25,000 people and enough souped-up Triumphs and Volkswagens to fill Max Yasgur’s farm.