Inside a haunted jail restaurant, we find a menu peppered in jailbird lingo. Diners at the Calaboose Grille experience a retrofitted cell and order “Grand Jury Wraps,” “Arresting Sandwiches” or a “Bugsy Siegel Veggie Burger.”

Welcome to Owego village, a resto in a county that doubles as the gateway to the Southern Finger Lakes region.

SMALL-TOWN VIBES

Owego in Tioga County is one of those New York state sleepy hamlets. Shops offer homemade frills and antique accents enticing patrons to kick back and browse. Homeowners proudly tend to their immaculately restored properties, many of which are heritage mansions. Meanwhile, the tavern keeper is reviving the village’s heritage flagship watering hole, turning it into a modern-amenity masterpiece, which should surely lure the crowds once completed later this year.

Who knew this small town, one of many situated in the Finger Lakes region, is laden with one-of-a-kind finds in the most unusual places. Owego has once even snagged the “coolest small town” title. Fronting the majestic Susquehanna River, the streetscape resembles a Norman Rockwell painting.

Situated in the heart of the Empire State, the Finger Lakes region offers a rich range of activities. Set your sights on the 1,046 kilometres of shoreline, hit more than 3,000 kilometres of biking and hiking trails, explore the Finger Lakes National Forest or, if antiques are more your style, follow the Antiques Trail in Tioga County. Laden with vineyards, rolling farmland, waterfalls and culturally rich towns, central New York is blessed with the famous 11 sinuous lakes.

While you might not experience them all on a weekend getaway, it sure is a goal worth pursuing on a country road trip. After scouring the two big daddies of the Finger Lakes, namely Seneca Lake and Cayuga Lake, I decided we didn’t need a game plan to experience one of America’s favourite haunts. We were like Thelma and Louise hitting a freedom trail of sorts as we never knew what we’d see along the way.

MORE SURPRISES

On the southeast side of Seneca Lake at the Stonecat Café, the brunch crowd was at full tilt. The casual restaurant is the incarnation of executive chef Scott Signori, a self-described organic cuisine crusader who’s been given the informal title, “Hero.” Wine Spectator has also noticed his Finger Lakes vinifera commitment.

The retro-clad servers looked like a vintage throwback to when this location once thrived as a fruit stand. Brunch was sublime. A garden basket of fresh figs, mixed greens, edible flowers from Flower Power—a local producer—were topped with shavings of artisanal goat cheese sourced only 20 minutes away. We washed down the light lunch with a garden-to-glass of Chardonnay produced around the bend at Ravines. Wine lovers frequently visit the family-run Ravines along the Seneca Wine Trail, one of the wine trails in the region. I literally savoured a Finger Lakes sensory tour without leaving the table.

Down the road with an impeccable view of the lake, a golden barn popped up before us. We hit the brakes. The SkyLand Art Barn is a treasure chest of handicrafts and heirloom pieces thoughtfully presented. It feels like Grandma stepped away momentarily. Inside the 1790s refurbished barn every nook and cranny is filled with art. “I want my place to reflect a hideaway where anyone is welcomed to browse and enjoy the ambience,” said Barbara Hummel, artist entrepreneur extraordinaire who has managed to revive two historic structures in one out-of-this-world experience. The other ancient treasure, a restored seven-room rental property (c. 1790), is popular with the weddings and family-reunion crowd.

Is it any wonder National Geographic Traveler once rated her one-stop shop featuring the works of 300 artists as one of the must-see sights in the state? I took my purchases, satisfied that a little pre-holiday shopping was such a cinch.

CRYSTAL CITY

Dubbed America’s Crystal City for the renowned Corning glass manufacturing, Corning is known as the town that glass built. Visitors sneak inside the charming downtown shops while culture buffs dive into the Rockwell Museum, the only Smithsonian Affiliate in Upstate New York for art exploration.

Although the downtown area is quite walkable, I hopped on board a free shuttle to the Corning Museum of Glass so I would have more time to enjoy Corning’s top attraction. This House of Glass boasts the world’s most important collection of glass spanning 3,500 years. Groups converged at a new amphitheatre to view glassmaking demonstrations while family and friends observed a massive tower of glass casserole dishes that seemed to float magically into thin air.

Later, enlightened shopkeepers in the historic downtown Gaffer District offered a stream of tips. Like everywhere in the Finger Lakes region, the small-town hospitality abounds. Steeped in a New England-like 1980s setting, a laid-back friendliness feels familiar yet homey like Cheers wrapped in St. Elmo’s Fire. For dining I ducked into a trendy restaurant with a chic urban flair, one of the earlier recommendations. It didn’t disappoint. The Three Birds Restaurant was packed. Afterward we went to the Palace Theatre, where cinephiles gather to watch first-run films. I was in luck. That evening Victoria and Abdul starring Judi Dench playing Queen Victoria hit the silver screen.

WINE COUNTRY

The next day at Lucas Vineyards and Winery, home of Nautie Miss Chevious, an unoaked Chardonnay, we clinked our glasses together. “We are three generations of women leaders,” explained the bartender describing Cayuga Lake’s first winery.

World-class wines hug the terra firma around the deep blue waters of the glacially formed lakes with their sloping shorelines. The recipe for success includes a cool climate ideal for delicate vinifera grapes like Riesling, bold Cabernet Franc or mellow Pinot Noirs. 

We drove beneath blazing tree canopies of bronze and gold until the outline of a building complex—the size of a football field—emerged at the valley floor. Foot on the brake, we slowly descended into the hollow. Our next break is considered the region’s oldest winery and there was another surprise.

At the Pleasant Valley Wine Company museum, a life-size cutout of hip-hop sensation Nicki Minaj appeared among the yesteryear bric-a-brac. The historic winery bottles her alcoholic bevvy, the Myx Moscato.

“Wow, how hip are we?” we laughed, taking the prerequisite selfie then shuffling off to the bar for the prescribed tasting.

Back in Owego, we had a game plan. Freshen up at our bed and breakfast, then saunter off to dinner where the movers and shakers hit the blackjack tables. Still, priorities prevailed. It was time to mellow out at the August Moon Spa on our final detour. Like Thelma and Louise, we discovered our ultimate getaway...minus the movie ending.

Travel Planner

For free self-guided Owego walking tours, call 607-354-4080. Upcoming spring events include the Seneca Lake Spring Wine and Cheese Weekend, April 20–22, and GlassFest (GlassFest.org), a four-day glass festival from May 24–27. More information on the Finger Lakes in Upstate New York is found at:

Cayuga Lake Wine Trail: cayugawinetrail.com

Finger Lakes Wine Country: fingerlakeswinecountry.com

New York’s Finger Lakes Tourism Alliance: fingerlakes.org

Seneca Lake Wine Trail: senecalakewine.com

Steuben County Conference & Visitors Bureau: CorningFingerLakes.com

Tioga County Tourism: experiencetioga.com

Tioga Downs Casino Resort: tiogadowns.com