Best Driving Vacations: Chautauqua's Slice of America

Lynn Freehill-Maye
Students work on perfecting their sailing skills.

It’s been called everything from “the most American thing in America” by the ever-patriotic Teddy Roosevelt to “summer camp for adults” by repeat millennial visitor Sarah Gamble. The old-fashioned lakeside town of Chautauqua, New York, has a 150-year history of inspiring the people of the United States, and the summertime fun and learning continue today. The place is essentially home to the original open-air TED Talks, with boating, swimming and other entertainment nearby.

Quick history lesson: In 1874, a Methodist group founded the town of Chautauqua as a tent-revival camp for Sunday school teachers. Their movement caught fire nationally. Its leaders sent lecturers to Chautauqua-affiliated assemblies around the country. The nation’s prominent thinkers became Chautauqua fans. Franklin D. and Eleanor Roosevelt stopped by often. Thomas Edison summered there. George Gershwin finished “Concerto in F Major” in one of its shacks.

The name Chautauqua still calls to mind thoughtful reflection for literary types like writer Robert M. Pirsig, who praised it in “Zen and the Art of Motorcycle Maintenance.” Pirsig wrote of “the traveling tent-show Chautauquas that used to move across America ... an old-time series of popular talks intended to edify and entertain, improve the mind and bring culture and enlightenment to the ears and thoughts of the hearer.”

The traveling 10,000-person tent shows may have died out, but Mother Chautauqua endures as today’s Chautauqua Institution, still hosting a stimulating nine-week summer program of lectures and performances. From June through August, everyone from Hillary Clinton to Wynton Marsalis is likely to turn up as this quiet lakeside village suddenly vibrates with energy. Recently, Dan Aykroyd met fellow comedian Lewis Black for the first time right there on a historic Chautauqua porch.

Understand that the institution is the town—in season, you must purchase a gate pass that admits you to the programming in order to enter Chautauqua. The village is arranged around a green quad, Bestor Plaza. The stately brick Smith Memorial Library anchors it at the south end, with a balcony providing sweet views of the park and the cafés and shops around it.

Multiple generations of families often vacation there together, since the institution also coordinates the Children’s School. The kids’ programming relates to the adult subjects, so families can come together at night with dinner-discussion topics in common. Chautauqua isn’t all serious business, though. A roster of recreational options—exercise classes, art courses and plenty of sports and games—are also offered.

“Whether you’re 2 or 102, there is something for you at Chautauqua,” says Jordan Steves, the institution’s director of strategic communications and community relations. “What makes it special are the intergenerational experiences we offer and the eclectic mix of programming. The feel here is very steeped in history, but it’s not a place that’s stuck at any moment in time.”

Learning Opportunities

Each week of Chautauqua’s programming falls under a different theme, as broad as “Shifting Global Power” in 2019. Sometimes the topics feel more relevant than organizers could’ve even planned—during last year’s Russia week at Chautauqua, Russian Prime Minister Vladimir Putin and U.S. President Donald Trump met in Finland for their world-order-upending summit. This year’s anticipated speakers include NPR’s Ira Glass, who headlines a week on storytelling.

Former Ohio Gov. John Kasich will appear during the “Uncommon Ground” week, scheduled during July Fourth. If you feel patriotic, Independence Day is an inspiring time to visit—residents decorate their porches with Uncle Sams lit up like Christmas trees, and enormous American flags hang from the balconies and old-growth trees. At night the Chautauqua Symphony Orchestra makes the institution’s big amphitheater, “the Amp,” boom with Sousa marches.

A 2019 highlight will be “What’s Funny” week, organized in partnership with the National Comedy Center, which opened in Chautauqua County last August. It’ll take humor seriously, examining what makes us laugh. The week’s end will coincide with the Lucille Ball Comedy Festival, a celebration of the comedian in her nearby hometown of Jamestown, allowing visitors to let loose by catching stand-up, taking improv classes or attending the gala.

Beyond the theme weeks, Chautauquans propose classes that anyone can take. A few of last year’s favorites: Better Camera Phone Photography, Mediterranean Spice Blends, the Art of Bookbinding, Intro to Filmmaking and Freshening Up Your French. Exercise classes such as yoga, Zumba and tai chi fill up fast, too. Witnessing a nonagenarian balanced in a yogi’s tree pose isn’t an unusual sight.

Lakeside Fun

With narrow streets and cars left in a big lot (for around $10 per day), everyone walks everywhere in Chautauqua. Visitors swim, sail and even lawn-bowl along the lake. Residents host parties on Victorian front porches. With walkability in vogue these days, Chautauqua is so old it’s new. “Chautauqua may be one of the original walkable communities,” Steves says. “Recreation is just sort of built into the rhythm of a day.”

Opportunities abound to get out on the water of the 20-square-mile Chautauqua Lake. The lake’s resident old-fashioned steamer, the Chautauqua Belle, stops at the dock. The sleek, modern Summer Wind yacht also motors around the lake. Canoeing, kayaking and paddleboarding are available. Chautauqua hosts an active sailing program, with classes for all skill levels.

Other activities around the county often share Chautauqua’s “leisure learning” feel. “The organizations outside the institution have adopted that recreational learning,” says Megan Arnone, marketing coordinator for the Chautauqua County Visitors Bureau. “You could take a foraging workshop, learning about edible plants and flowers, or you could join in on a guided nature walk.”

Nature walks are often arranged through Long Point State Park or by staff of the Roger Tory Peterson Institute of Natural History in the ornithologist’s birthplace of Jamestown. The late U.S. Supreme Court Justice Robert H. Jackson, who facilitated the Nuremberg trials for Nazi war criminals, practiced law in the area for 20 years. His namesake, the Robert H. Jackson Center, now hosts year-round speakers on topics like constitutional amendments or human rights issues, often partnering with the Chautauqua Institution.

Around the County

Jamestown isn’t in the middle of nowhere for a national museum—it’s “within 500 miles of two-thirds of the U.S. population,” Journey Gunderson will have you know. Gunderson is the executive director of the new National Comedy Center. This year, many Chautauqua visitors are expected to check out the state-of-the-art museum just 16 scenic, lakeside miles southeast, in Lucille Ball’s hometown. “Now that we’ve built it, I can see why no one has done this before,” Gunderson says wryly. “Because it’s very hard.”

See what $50 million will buy—a facility that not just comedians and their mothers have been calling the best museum in America. The exhibits are so hyper-interactive, a wristband will tag your sense of humor (dark? satirical? situational?) and deliver more of what’ll crack you up. You can do a Laugh Battle in which sensors will use facial recognition technology to give you points for making your opponent laugh. At the end there’s Comedy Karaoke for anyone brave enough to stand up and deliver stand-up. (Yes, there’s a bar.) You can take Lewis Black’s example and (fondly) roast Chautauqua itself: “If there was ever a place that was ripe for being made fun of, it’s here, where it’s so idyllic and precious, it can leave one mildly nauseous.”

A final educational fact: Chautauqua County is the biggest Concord grape-growing region in the world. European wine varietals grow well in the area’s 30,000 vineyard acres, because the ridge along Lake Erie keeps it all temperate. Chautauqua is also becoming known for breweries and “farm distilleries,” which source at least 75 percent of their agricultural inputs from the state of New York.

Five & 20 was the state’s first producer to make wine, beer and spirits. Southern Tier Brewing Co. started in Lakewood (where tours of its flagship facility are offered on Saturdays), and the company now has a distillery as well. Ellicottville Brewing Co. has taproom locations in the county, too. So it’s a breeze imagining how to close out a summer in Chautauqua: by having a drink, sharing a laugh and holding forth on some of your newfound knowledge.

Lynn Freehill-Maye is a writer based in upstate New York who fell for Chautauqua while living in Buffalo.


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Rooming houses and rentals: Lodging within Chautauqua’s grounds ranges from comfy hotels to full-house rentals to basic, shared rooming houses. The institution employs an accommodations manager to serve as concierge for guests not already familiar with the setup. Email Christine Boniface at

Chautauqua Harbor Hotel: This summer, the former site of the Celoron Amusement Park (where Lucille Ball got her start) will host an expansive new Arts and Crafts-style hotel on the lakefront. Grand and resortlike, it’s just a 15-mile drive south of the Chautauqua Institution.

The Athenaeum: The Chautauqua Institution’s grande dame hotel is a Second Empire beauty with ample verandas and old-fashioned keys. But the 154-room Victorian property has also been getting updates. As of last summer, it opened a full bar for the first time; guests are now welcome to enjoy a drink on the porch.

Camp Chautauqua: Budget travelers looking to immerse themselves in Chautauqua County’s nature will appreciate this family-operated campground. The land holds both tent sites and concrete RV pads, and kid-friendly features include a swimming pool and petting farm.

Where to Stay