Explore upstate New York's hidden gem small towns for a fall getaway

New York is rich with small towns that deserve more attention. Steeped in history, these little villages in the Catskills, the Hudson Valley and the Finger Lakes region beckon with fascinating spots to explore, from a museum dedicated to all things Oz to a Mennonite crafts market and a bed-and-breakfast at a llama farm. Almost all have a charming Main Street offering plentiful retail therapy, outdoor activities like hiking and biking, and most importantly, the chance to relax and disconnect.

"The small-town vibe is really special in these little villages," said Melaine Rottkamp, president of the Hudson Valley tourism board. "It’s because the people are really special," she added, noting that everyone is so happy to share the unique things about their towns with travelers. And she notes, tourists can find wonderful restaurants in many of these spots. A James Beard finalist has a restaurant in Pine Plains, she said. Other culinary hot spots include Isabela in Amenia, run by a chef who once earned a Michelin star, and the restaurant at Troutbeck, a hotel in Amenia that sources much of its food from local farms.

Even the names are intriguing, so take a drive and explore charming spots like Chittenango, Goshen and Penn Yan.

Chittenango

DRIVING DISTANCE FROM LI: About 5 hours 

The development of this little village in Madison County can be attributed to the growth of the Erie Canal, which linked Buffalo and Albany. Travelers can visit the Chittenango Landing Canal Boat Museum, where cargo boats were built in the 19th century. The Wild Animal Park has an impressive collection of creatures, among them tigers and leopards. Mostly visitors come for the yellow brick roads — the village is the birthplace of "The Wonderful Wizard of Oz'' author L. Frank Baum, and yes, many of the town’s sidewalks are yellow. There’s an annual Oz Festival in June and The All Things Oz Museum has a wealth of memorabilia, including original props from the movie.

OVERNIGHT STAY There are few hotels in town, but the historic Lincklaen House (room rates starting at $115) in nearby Cazenovia is a charming hotel with 22 guest rooms. Think comfort food with a southern flair at Ruby Begonia’s.

Goshen

DRIVING DISTANCE FROM LI: About 2 hours 

Smithsonian Magazine named this village that dates to the 1700s one of the best small towns in the United States. The Hudson Valley town is a perfect family destination, mostly because of the colorful theme park Legoland, where seven lands feature rides ranging from thrilling to chill. Families also love the Goshen Heritage Trail, a 19.5-mile path on a converted bed of the Erie Railroad that wanders past a bird sanctuary, historic landmarks and flowing steams. Racing enthusiasts will want to check out the Harness Racing Museum and Hall of Fame, which honors both people and horses who participated in the sport. Races still take place at the historic track throughout the summer.

OVERNIGHT STAY Many rooms at the Legoland hotel (rates vary by date; family size) have separate sleeping areas for the kids, and the hotel also offers nightly entertainment and daily breakfast at the highly rated Bricks Family Restaurant. Add a little luxury to the weekend with dinner on the patio at the charming Stagecoach Inn.

Hammondsport

DRIVING DISTANCE FROM LI: About 5 hours

This small village on Keuka Lake played a huge role in the nation’s aviation development. The first seaplanes, built by Glenn Hammond Curtiss, took off in 1912, part of the history on display at a local museum named for the aviation pioneer (curtissmuseum.org).  You’ll also see vintage motorcycles — Curtiss started out as a bike messenger and went on to build motorcycles.  At the Finger Lakes Boating Museum, you can learn about early steamships built in the region, watch boats being restored, and tour the lake on the Pat II ferry. These days, the town is best known for its many wineries and breweries, among them Dr. Konstantin Frank Winery, where tastings take place in the winemaking pioneer’s former home, and Bully Hill Vineyards, where a gallery features the owner’s artwork.  

OVERNIGHT STAY The Black Sheep Inn (rooms starting at $220) is a five-bedroom bed-and-breakfast offering plant-based food, with amenities like picnic lunches and rides to nearby wineries. Eat a light meal or grab a treat at Crooked Lake Ice Cream Co.

Kingston

DRIVING DISTANCE FROM LI: About 2 hours and 30 minutes 

The state’s first capital, at the confluence of Roundout Creek and the Hudson River, is rich in history.  But there’s also a vibrant arts scene, including the vivid murals found in the midtown arts district, and the Ulster Performing Arts Center, with everything from ballet to jazz.  History buffs can take a guided tour of the 1658 stockade historic district, which includes architecture by the late Director-General Peter Stuyvesant.  Every other year, the town re-enacts the events of 1777, when the British burned most of the town’s buildings. There are many ways to explore. Take a mile and a half trolley ride through downtown at the Trolley Museum of New York, ride through Hudson Valley farmlands on the Catskill Mountain Railroad or, through October, board the Rip Van Winkle II for a narrated sightseeing tour on the Hudson. 

OVERNIGHT STAY Hotel Kinsley (rooms starting at $290) features a restaurant and a bar for those looking for a weekend getaway. For light bites and an interesting selection of “low intervention” wine, check out Brunette.  

Penn Yan

DRIVING DISTANCE FROM LI: About 6 hours

Once a shipping hub, this village on the shores of Keuka Lake takes its name from Pennsylvania and Yankee, in honor of its 18th century settlers. With rolling hills and stunning lake views, the town is often called New York’s "little Tuscany." The gateway to the Finger Lakes region, it’s a solid destination for touring wineries or hiking the 7-mile Keuka Lake Outlet Trail, which will take you past Seneca Mills Falls. Mennonite families who have located to the region showcase their wares at local craft markets, among them the Windmill Farm and Craft Market, open until the last weekend in November and selling everything from furniture and art to baked goods. Learn about the history of the region at several museums that make up the Yates County History Center.

OVERNIGHT STAY Fresh fruit and vegetables from their own gardens highlight breakfast at Los Gatos, (rooms starting at $189) a bed-and-breakfast with several rooms and two log cabins.  Honor the town's boating heritage with lunch or dinner at the Main Deck, offering locally grown comfort food and views of the lake.

Phoenicia

DRIVING DISTANCE FROM LI: About 2 hours and 30 minutes 

At the foot of several well-known state mountains (Mount Tremper, Romer and Sheridan), this Ulster County hamlet is becoming known for its focus on wellness. The town is dotted with shops selling spiritual rocks, minerals and crystals. Menla Retreat & Dewa Spa hosts regular retreats focusing on yoga and Buddhism, and some treatments are based on the restorative therapies of Tibet. For a more active approach to wellness, hike the Tanbark Loop Trail (steep and narrow, best for experienced hikers) or bike the Catskill Scenic Trail. Take a break with a visit to the Empire State Railway Museum.

OVERNIGHT STAY The Graham & Co. (rooms starting at $130) is a 20-room boutique hotel with fire pits and bikes to borrow. Fans of the Apple+ show "Severance" will want to eat at the Phoenicia Diner, which was used as a set in several episodes.

Roscoe

DRIVING DISTANCE FROM LI: About 2 hours and 20 minutes 

This charming hamlet in the Catskills calls itself Trout Town, USA. Fly fishing enthusiasts are lured (sorry, couldn’t resist) by the convergence of two rivers, Beaver Kill and Willowemoc Creek. The hot spot is Junction Pool, thought to attract trout that linger because they’re confused by the unpredictable currents. The Catskill Fly Fishing Center and Museum looks at the history of fly fishing and has a workshop for tying flies and making bamboo rods. Other popular sights include the Beaverkill and Livingston Manor covered bridges. Grab a brew at Roscoe Beer Co., where you can sip suds and see trout decor. 

OVERNIGHT STAY Buck Brook Alpacas (three night minimum; rates vary) has turned the space above the barn into a cozy B&B (if it’s booked, you can still tour the farm or schedule an alpaca walk). The Roscoe Diner has been feeding travelers since 1962, a frequent stop for people heading up to visit upstate colleges.

Westfield

DRIVING DISTANCE FROM LI: About 7 hours 

Known as the Concord Grape Capital of the world, this town sits on the western shore of Lake Erie, where visitors can chill on multiple beaches, or hike the shoreline to the historic Barcelona Lighthouse. For the truly adventurous, divers can explore several shipwrecks, among them the Washington Irving, a freighter that mysteriously sank in 1860.  Nearby, the Chautauqua Institution is a renowned cultural and educational arts center, while the National Comedy Center is a fun museum that honors local citizen Lucille Ball. But the heart of the town is the production of Concord grapes, dating to 1897, when Charles E. Welch moved his company from New Jersey, lured by the promise of optimal climate conditions. At the Lake Erie Grape Discovery Center, visitors can learn about the history of grape growing, then sample various wines and juices on the patio.  

OVERNIGHT STAY The five-room Barcelona Lakeside B&B (rooms starting at $179) is right across from the beach and offers several hiking and winery packages. For some homemade cooking, try Jack’s Barcelona Drive-In, where the lake’s fresh perch gets raves.