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If you are planning a trip to the Empire State, you are better off escaping the clichés and the glittering chaos of New York City. Why not make a trip up north to Upstate New York, where towns host fantastical festivals celebrating everything from garlic to gnomes? If that's not your cup of tea, you can step into sleepy villages with streets paved with poetry and legends that permeate an air of whimsy.

Whether it's a village famed for its spiritualist past or a hamlet where the desserts are as sweet as the scenery, the unusual is usual, and the ordinary is extraordinary in these eight notable small towns. Pack your bags, bring your imagination, and uncover the whimsical heart of Upstate New York.

Cooperstown

Cooperstown, "America's Hometown," truly encapsulates the whimsical and quirky essence of a small town deeply entrenched in America’s favorite pastime—baseball. Best known for housing the revered National Baseball Hall of Fame and Museum, Cooperstown offers visitors a chance to walk through baseball history with exhibits that celebrate legendary players and the Plaque Gallery, where bronze plaques immortalize baseball’s greatest. However, the town's quirkiness extends beyond the outfield; Doubleday Field, nestled within the town and steeped in lore as baseball's birthplace, hosts numerous games and events that capture the heart of the sport in a setting that feels like stepping back in time.

Beyond the baseball diamond, Cooperstown's whimsy is amplified by the Farmers' Museum, the oldest living museum in the U.S., which offers a glimpse into the agrarian lifestyle of the mid-19th century. This museum, along with a trolley ride to Main Street, the bustling hub of the town, adds layers to the town’s whimsical personality. Main Street itself is a picturesque tableau of small-town America, lined with quaint shops and cozy bed-and-breakfast inns that beckon visitors to explore and relax.

Roscoe

Roscoe, self-dubbed as "Trout Town," has a history as a haven for fly-fishing enthusiasts due to its prime location at the Beaver Kill and Willowemoc Creek confluence, shaping much of its character and charm. This reputation not only attracts anglers from around the globe but also enhances its rustic appeal, showcased by the community's dedication to preserving its natural beauty and recreational draw. Beyond fishing, Roscoe's historical roots add layers of intrigue; it was once the home to the Delaware Indians and known as Westfield Flats, where wolves once roamed in the open. The transition from a Native American homeland to a vibrant settler community is commemorated in places like the Westfield Flats Cemetery, adding a poignant reminder of the town’s layered past.

Moreover, Roscoe's appeal extends into its vibrant local scene, marked by the famed Roscoe Diner and its bustling Spirit, Brew, and Wine Trail. The town’s eclectic mix of establishments, from the Do Good Spirits to the Roscoe Beer Company, provides a lively cultural fabric that appeals to both residents and visitors alike. Adding to its allure are the various craft stores, antique shops, and sporting goods stores that line its quaint streets, inviting guests to explore and discover.

Chittenango

Chittenango, the birthplace of L. Frank Baum, the author of "The Wizard of Oz," takes its Oz heritage seriously, with yellow brick sidewalks and an abundance of Oz-themed attractions that delight both the young and the young at heart. The All Things Oz Museum is a treasure trove of memorabilia from the Oz series, offering a deep dive into the magical º£½ÇÉçÇø Baum created. Each year, the town's Oz-Stravaganza festival in June draws fans from across the globe, celebrating the legacy of the Oz books and films with parades, performances, and guest appearances from descendants of the original movie's cast. Furthermore, the Yellow Brick Road Casino provides a playful nod to the famous story, offering entertainment and dining amidst decor inspired by the Emerald City, ensuring that the spirit of Oz is palpable at every turn.

Beyond the glitter of Oz, Chittenango also embraces its picturesque natural setting along the Erie Canal and the dramatic backdrop of the Chittenango Falls State Park. The park, with its stunning waterfall and lush nature trails, offers a serene escape, allowing visitors to enjoy the peaceful beauty of Upstate New York. The town's involvement in the Haunted History Trail of New York adds another layer to its appeal, with local lore and eerie tales that contrast with its storybook charm.

Lily Dale

Founded in 1879 as a summer retreat for spiritualists, this village has grown into a bustling hub where visitors from all over the globe come to connect with the spirit realm. The town’s foundational belief that the dead can communicate with the living permeates every aspect of its culture, from the daily activities to the architecture. Lily Dale is home to numerous board-certified mediums who conduct readings and spiritual classes, drawing thousands annually to this mystical enclave. The town's dedication to spiritualism is a cultural identity and an invitation to explore the unseen, making it a hotspot for those seeking otherº£½ÇÉçÇøly experiences.

Visitors often find themselves at the Forest Temple attending group services or exploring the Lily Dale Museum, where they learn about the town's intriguing visitors, like Deepak Chopra and Susan B. Anthony. A walk through the wooded paths leads to Inspiration Stump, a locale believed to be charged with spiritual energy, and the nearby Lily Dale Pet Cemetery, where the graves date back over a century, adding a peculiar twist to the town’s narrative.

Old Forge

As one of the region's top tourist destinations, Old Forge offers a vibrant main street lined with artisan shops and quaint eateries. Among them is the beloved Old Forge Hardware, known as “The Adirondacks’ Most General Store, as it epitomizes the small-town charm with its old-timey vibe and an array of goods that seem to transport visitors back in time. Moreover, the town is famed for its Enchanted Forest Water Safari—New York’s largest water park, which adds a layer of enchantment to the area. Moreover, events like Paddlefest, which celebrates kayaks and canoes, and the festive Winter Carnival invite tourists to immerse themselves in the community’s spirited celebrations and seasonal activities.

The town serves as a gateway to the Fulton Chain of Lakes, offering abundant opportunities for water sports and serene lake views. For a unique perspective on the region, the Adirondack Scenic Railroad provides a nostalgic journey through the rugged wilderness, allowing passengers to experience the beauty of the mountains from the comfort of a vintage train. Nearby, McCauley Mountain transforms with the seasons—from a ski paradise in winter to a picturesque backdrop for hiking and mountain biking in the summer.

Phoenicia

Phoenicia offers unique attractions such as Rail Explorers, where visitors can rent bikes to pedal along the scenic paths of the old Ulster and Delaware Railroad, paralleling Esopus Creek. Phoenicia's array of trails also beckons the active traveler, with routes leading to stunning natural landmarks like Giant Ledge, Kaaterskill Falls, and Overlook Mountain. Between explorations, visitors can refuel at local favorites such as the iconic Phoenicia Diner or Brio’s for some artisanal pizza, ensuring they have the energy to soak in all the natural beauty and quaint local culture that Phoenicia has to offer.

Phoenicia comes alive with a creative vibe, particularly in the summer when it fills with tourists and hosts the Shandaken Artist Studio Tour and The Festival of the Voice, drawing both local and international talent. For accommodations, spots like the nearby Urban Cowboy Lodge offer a modern twist on rustic lodging, complete with in-room clawfoot tubs for a touch of luxury in the wilderness.

Sharon Springs

Sharon Springs has gracefully transitioned from a famed 19th-century spa destination to a charming, modern-day tourist spot. This town's revitalization is most apparent in its historic district, where visitors can admire a collection of beautifully restored buildings that whisper tales of its opulent past. The American Hotel, dating back to the 1840s, now serves as a boutique inn, offering guests a glimpse into the luxury that once drew crowds from across the country. A stroll down the town's main thoroughfare presents an array of locally owned shops and eateries, including the popular Black Cat café, which sits conveniently across from the American Hotel. This mixture of historical architecture and contemporary culture crafts a picturesque setting that invites leisure and exploration, enhanced by visits to the Sharon Historical Society Museum, where local lore and artifacts add depth to the visitor's experience.

The town's former spa glory is echoed in the remnants of grand hotels and bathhouses that line the streets, offering a haunting beauty that captivates the imagination. Modern Sharon Springs also thrives with unique local businesses such as the Beekman 1802, renowned for its high-quality, locally sourced products and national media attention. For those inclined toward natural wonders, the nearby Howe Caverns provide a spectacular underground adventure featuring limestone caves and guided tours that reveal the region's geological history.

Le Roy

Le Roy is recognized as the birthplace of Jell-O, adding a delightfully sweet layer to its cultural identity. This small village, nestled at the intersection of State Routes 5 and 19, carries the charm of a classic American small town with a twist of the unexpected. The annual Oatka Festival, a summer event started in 1989, showcases Le Roy’s rich culture and history, featuring local vendors, businesses, and restaurants that come together to celebrate the community spirit. This festival highlights the town's culinary delights and underscores its strong community bonds and pride in its unique heritage, making it a standout destination for those seeking the peculiar and charming.

Le Roy is home to several sites listed on the National Register of Historic Places, such as the First Presbyterian Church, the Keeney House, and the Machpelah Cemetery, each offering a glimpse into the village's storied past and architectural beauty. These historic sites, alongside modern-day attractions, create a dynamic atmosphere where history and contemporary culture intersect.

End Your Whimsical Journey

Upstate New York's whimsical towns are worthy destinations for all kinds of visitors, offering a unique blend of history, charm, and unexpected delights. Whether you're drawn to Le Roy's Jell-O fame, Sharon Springs' nostalgic spa days, or the magical streets of Chittenango, there's something for everyone in these quirky small towns. Each town invites you to uncover a special piece of Upstate New York’s heart, where the ordinary becomes extraordinary. So pack your bags and embrace the adventures awaiting in these eight remarkable destinations—your imagination will thank you.