11 Most Laid-Back Small Towns in New York
The laidback vibes get stronger away from the Big Apple through picturesque landscapes, from the Finger Lakes to the Adirondacks and Hudson Valley. Calling to unwind in every season, the small hubs of culture and history accentuate the great outdoors with unique beauty and a blend of attractions. Just in time for harvest, taste along the most saturated wine trail and rustle through the colorful state park in Watkins Glen on the southern end of the largest Finger Lake.
Ithaca is home to the Ivy League school and some of the state's best restaurants. The agricultural bounty of the Hudson Valley extends to Saugerties' famed garlic festival, which is sure to ward off any vampires in time for Halloween. For a wintertime escape, how about skiing in Ellicottville, home to Holiday Valley Resort, a premier destination for snow sports?
Canandaigua
Just 25 miles southeast of Rochester, on the north end of Canandaigua Lake, Canandaigua encourages visitors to recharge and refresh with the power of nature. Once a Seneca village of refugees from the nearby Ganondagan, destroyed by the French in 1687, the Europeans from eastern New York and New England settled in after the Phelps & Gorham Purchase in the late 1780s. A town since 1791, the Treaty of Canandaigua, signed in 1794, established clear boundaries, ensuing peace between the new citizens and the six nations of the Iroquois Confederacy. Its own entity since 1815 and incorporated almost a century later, the village of Canandaigua today attracts tourists with a "quaint, down-home demeanor."
Translated as “the chosen spot” from a native language, it really is a stunning place. Enjoy swimming, boating, fishing, and picnics along the beautiful lake's shore, with handsome cottages where the late Humphrey Bogart spent childhood summers nearby. Historic facades form an appealing downtown, together with local shops, galleries, and restaurants. Centered around a grand 1800s mansion, the historic Granger Homestead and Carriage Museum depicts colonial life along expansive grounds with carriage and sleigh rides. Next door, stop by the Fort Hill Performing Arts Center while the exotic fauna and trails through Sonnenberg Gardens and Mansion State Historic Park inspire a fairytale in saturated colors.
Catskill
Although the Catskills are considered a trendy spot in the face of the roughneck Adirondacks, this small town offers a chance to hunt for beauty and adventure through the great outdoors and relax in the downhome feel with few crowds. As one of the state's most overlooked towns for nature lovers, the artists, writers, and other creative types among them draw inspiration from the tranquility of stunning forest hikes and the adrenaline rush of summiting the high peaks. From its own miles of mountain biking trails through the Catskill Preserve to the sparkling blue lakes, see the carpeted mountains light up on fire after the early fall adventurers have had their fill along the colorful rug. The Hudson River School Art Trail features Thomas Cole's 19th-century paintings.
Many enjoy an open-air ride on the Catskill Mountain Railroad, while the Upper Delaware Scenic Byway takes you along dramatic vistas and quaint villages just in time for the leaf-peeping season. Shoot northwest to East Durham for the last summertime hoorah in a beautiful mountain setting at Zoom Flume Water Park, perfect for family fun. Rustle through the fallen leaves of late fall, with stops to shop like Willa's for a bite, next door to the Avalon Lounge, a music venue for the evening. Dutchman's Landing Park features a playground where parents can relax and enjoy the flow of the Hudson River. Cross the Rip Van Winkle Bridge to Olana State Historic Site in Hudson, which offers exhibits through the grand estate and studio of painter Frederic Edwin Church.
Cooperstown
What could be more laid-back and exciting at the same time than America's favorite pastime? This Upstate NY town, home to the National Baseball Hall of Fame and Museum, is a hub for baseball culture along the southern shore of the beautiful Otsego Lake. The iconic institution offers a museum with a unique history of the sport worthy of the $30 entry fee to view memorabilia and sightsee the hall of fame, where fans line up during the annual induction ceremony of the latest league. Offering a culturally enriching getaway, discover the hardworking yet laidback farmer's lifestyle at the Farmer's Museum or view art at the vibrant Fenimore Art Museum. Just a stroll from downtown, scenic woodlands fringe the shoreline, with trails to stretch your legs and scavenge for wildlife.
For a full day in nature, Glimmerglass State Park just north along the lake offers hiking trails and beaches, while the annual Glimmerglass Festival attracts music and live arts fans for various lakeside performances at the Alice Busch Opera Theater. Break for a meal just south of downtown at Upstate Bar and Grill. Home to Council Rock Park, where Native Americans would allegedly gather by the view prior to the American Revolution, it is perfect for a refreshing stroll, a photoshoot, or a picnic in a beautifully calm yet exquisite place. Just downstream of the Susquehanna River, which flows through Cooperstown's heart, Fernleigh Estate Stone Bridge is a scenic hike with a historic brick bridge view. The hilltop Fairy Springs Park offers a serene spot at sunset, with a staircase descending to the lake.
Ellicottville
Coming alive under the snowflakes, this ski town in Western New York is a renowned wintertime escape with accommodations in the scenic foothills of the Allegany Mountains. Minutes south of downtown, Holiday Valley Resort is a premier destination for skiing, snowboarding, and tubing. Relaxing through the rest of the year, Ellicottville transforms into a hub for golfing, mountain biking, and zip-lining, with thought-out attractions that match every interest for a laidback getaway in any season. Explore McCarty Hill State Forest just south, with a number of ponds and wildlife viewing. The top-rated Dina's and Ellicottville Brewing Company offer a luxurious feel at fair prices for fine dining and the finest regional brews. For something more casual, Gin Mill is a family-owned tavern.
Attracting thrill-seekers in the warmer months, Sky High Adventure Park offers rope courses, tree-top walks, and family fun. Next to the sprawling Elmers Dog Park, the Nannen Arboretum is a beautiful place to relax amid ponds and plants. From Katy's Cafe in the morning to the casual Tim & Bonnies Pizza for lunch, explore the picturesque village with its tree-lined streets and historic buildings during Ellicottville Jazz & Blues Weekend or the Fall Festival, just a few of the regular events. For a memento, score a one-of-a-kind kitchen item from the in-house oven at Horn Hill Pottery and snap a selfie aboard the mountain coaster with foliage-ridden mountains all around and colorful patchwork in the palm of your hand.
Greenport
Greenport, once a seafarer's port and whaling ships' rest stop, was incorporated in 1838. Thousands of fishermen, shipbuilders, and farmers lived in the area by the mid-19th century. A prominent oyster processing location in the early 20th century and a thriving hub for rum running during Prohibition, Greenport is home to a handful of world-class wineries and soft-sanded beaches. Perfectly situated along the tip of Long Island’s North Fork, between the ocean and the bay, Greenport is a popular summer escape from busy NYC to watch sailboats glide by and go swimming at the scenic 67 Steps Beach. Offering nostalgic maritime views and attractions, stroll along the docks and enjoy whale watching or a sightseeing cruise. Inlet Pond County Park is a serene spot at sunset.
Next to the Hamptons, Greenport feels even more laidback with its country homes, historic architecture, and farmers’ markets in lieu of the wealthy mansions. Perfect for a budget escape, the Village of Greenport McCann offers a campground at its heart. The active can take out a charter for some deep-sea fishing, an explorative excursion, or meander the inlets along the rugged yet developed coastline for various views, like the Stirling Basin. Kontokosta Winery offers a quiet, relaxing evening with your loved ones. Next to the East End Seaport Museum, Claudio's Waterfront fixes hearty sandwiches and classic seafood dishes overlooking Greenport Harbor along a large terrace.
Ithaca
Ithaca, home to Cornell University, is an outgoing town with a relaxed collegiate vibe along its historic streets lined by brick buildings and leafy trees near the longest of the Finger Lakes, Cayuga. Centered around the prestigious Ivy League school, the heart of Ithaca Commons offers a fine selection of casual eateries, shops, bars, and cultural spaces. Steps away, Cornell Botanic Gardens beckons for a stroll, while the multi-tiered Ithaca Falls, one of the Empire's prettiest, is just a quick hike away. Both provide romantic backdrops for couples or family escapades. Resonating with something for every taste, the youthful vibe attracts visitors from around the nation for a quick escape, complete with top-notch arts and dining.
There's never a dull moment in Ithaca, most laidback in the summer to enjoy lakeside pursuits. From swimming and fishing to kayaking and boating with rentals at Taughannock Falls State Park, indulge in some of New York's best restaurants and attractions at student-oriented prices. The nearby gorges are an adventurer's playground, while plentiful art spaces indoors and outdoors, as well as regular live musical shows, keep the studious culturally entertained. From woodland walks and wildlife spotting to lake cruises, chase the scenery, catch up on R&R you've been putting off from behind the work desk, and get a comprehensive scope of the region with easy access to nearby towns and Buttermilk Falls State Park.
Livingston Manor
Some 100 miles from New York City, this lesser-known hamlet, “a small town with a big yard,” offers the great outdoors from the doorstep. Step onto a forest trail for a waterfall hike or relax by a number of ponds, with Round Top Trail and Rotary Park right in town. In honor of its world-famous fly-fishing streams and rivers, including Willowemoc Creek through the heart, Catskill Fly Fishing Center & Museum displays artifacts. Livingston Manor, "Catskills’ Newest Hotspot," according to Condé Nest, welcomes you to browse a vibrant spectrum of design, gifts, and outdoor shops, breweries, restaurants, bars, and even a world-class art gallery.
Power your exploration along the Parksville Rail Trail minutes south of downtown at Main Street Farm Market Cafe, or grab something to go from Peck's Market for a picnic by Beaverkill Covered Bridge. Robin Hood Diner has a woodsy appeal, while Dundas Castle is under a 15-minute drive north or a great day hike. Having experienced a recent influx of creatives and entrepreneurs from the city, Livingston Manor is an up-and-coming town perched high in the Catskills that is defined as "laidback." Home to around 800 people, living by the motto "leisure is excitement," join them at Upward Brewing Company. Sprawling in the northeast, Catskill Park is home to 100 mountain peaks and six major rivers, replete with wildlife including black bears and bald eagles.
Saugerties
Saugerties occupies a cozy spot in the Hudson Valley, between the Hudson River and Catskill Park. Its adventure-ridden face comes without a tourist hub feel but with a unique collection of antique stores and mom-and-pop shops that appease every rugged and casual nature lover. From the Catskill Animal Sanctuary, Falling Waters Preserve, and Esopus Creek Conservancy, reconvene downtown in its historic ambiance. Home to stunning 19th-century architecture, the circa 1869 Saugerties Lighthouse is a touchstone at the confluence of the Hudson River and Esopus Creek, accessible via a scenic half-mile trail. The abounding variety of landscapes makes Saugerties a renowned outdoor destination, like Esopus Bend Nature Preserve, perfect for birdwatching.
Built to guide ships along the river, the operating lighthouse doubles as a B&B to unwind over a picnic, a photoshoot, or a sunset. The Clermont State, a colonial circa-1750 mansion just north, offers tours, lush hiking trails, gardens, and river views along the 500-acre grounds. Saugerties is proud to host the Hudson Valley Garlic Festival and the 6.5-acre Opus 40, a stone sculpture park in an abandoned quarry with trails and a museum of vintage tools. The family-friendly festival celebrates the fragrant vegetable at the end of September, with roasted smells wafting from a number of vendors and fresh local cloves for sale. Many come to hike up the nearby Catskill Park, climb the nearby mountains, or enjoy camping in the summer. Chase the foliage on an easy riverside stroll this fall.
Watkins Glen
Named after the heart of the Finger Lakes Region, Watkins Glen State Park, this tiny town is one of the most popular summer escapes at the southern end of Seneca Lake. Home to leafy town greens and scenic trails, Catharine Creek Wildlife Management Area is immediately south. Take a hike to the spectacular Rainbow Falls or explore gorges, waterfalls, and hiking trails through the state park. Relax at Clute Park, home to play areas, a rentable pavilion, a skate park, and Seneca Lake Kayak. Eagle Cliff Falls and Cavern Cascade are an easy hike away. The outdoors will make you hungry to taste along its culinary and beverage trails, with museums, sports, and entertainment venues for time in between. Quintus Gallery offers collectible art from around the region, together with an inspiring space to retreat and create in workshops.
Built in 1828 as a tavern turned Select School for Boys, the boarding house and home of Dr. Charles D. Clawson, the Brick Tavern Museum is the oldest brick structure in Schuyler County. Road-racing fans enjoy NASCAR events and 3-lap tours to Watkins Glen International. Peppered with most wineries in New York along the western shore, Seneca Lake Wine Trail cultivates diverse, world-class wines through open-door, beautiful spaces for tastings, and lovely evenings spent with a glass in good company. Despite its weekly attendance exceeding 8,000 to 10,000 people, Windmill is the first farm and craft market in Upstate New York, some 20 minutes north of town in Penn Yan. Open through October, stock up on fresh vegetables, meats, flowers, baked goods, cheese, and pantry staples, as well as wine and unique crafts, all produced locally.
Westfield
This tiny, aptly named town is often overlooked on the western shore of Lake Erie in Chautauqua County. Coming alive during First Friday street fairs and Saturday farmers' markets, Westfield is a popular summertime escape from Buffalo or even Canada. Home to Barcelona Lighthouse, the nearby beach, and the harbor offers a range of lakeside pursuits, like fishing, sailing, and swimming, among a number of golf courses, waterfalls, and recreational trails. Here, at the heart of the world’s largest Concord Grape Belt, many farms and wineries offer tours and tastings year-round. Take a hike northward along the lake to Bournes Creek Falls, within a serene nature preserve, steps from Blue Water Beach Campground. Head south, and you'll hit Brookside Beach, another campground with an attraction in its name.
Venture inland to Fitch's Falls, an easy hike from Big Fill Tunnel, and detour along the highway to the cute Portage Hill Art Gallery in a complementing natural setting off the beaten path. Find more music, galleries, theater, and dance venues downtown that encourage relaxation after adventures. Switching into a leaf-peeping mode with foliage-ridden streets, stop by McClurg Museum in any season, in between shops, restaurants, and bakeries like the top-rated Portage Pie. This fall promises a vibrant drive along the Seaway Trail. Flaunting friendly businesses and a strong agricultural economic base, the internationally renowned Chautauqua Institution is minutes away with its bounty of cultural and learning opportunities on the history and natural resources of the region, home to the largest inland lake in Western New York.
Woodstock
Eliciting a bohemian vibe, Woodstock is a perfect small-town escape for all ages of art and music lovers, next door to Saugerties and near Bethel, where the iconic festival took place. Colorful and laidback, with good music and a photogenic collection of homes, unique boutiques, vegetarian restaurants, and laid-back coffee shops along the legendary Tinker Street, it has the magnetic effect of a Pleasantville. Fitting entirely within Catskill Park, the saturated colors of nature reminisce of its own hearty splash of tie-dye. Woodstock is a second-to-none fall destination for leaf-peeping adventures through its own Thorn Preserve-Catskill Center. Stop by Woodstock Artist Collective and the Sunfrost Farms for picnic provisions or a snack at the quirky Cheez-In Diner.
After hiking and biking in the park, the iconic Woodstock Playhouse has staged plays, musicals, concerts, and other artistic performances ever since 1938. The whole region has a calming feel, with a hamlet named Zeno to the east and Little Owl Japanese Teahouse offering a nature-centric escape in hotel-style accommodation due west. Nearby, Karma Triyana Dharmachakra Tibetan Buddhist Monastery flaunts idyllic grounds and offers welcoming meditation sessions. The Comeau Property is a spectacular open space to explore, with mountain views and nearby inns. There are many wonderful event locations, from Bearsville Theater to Levon Helm Studios, as well as Colony, which is a restored 1929 theater featuring diverse music acts, comedy, and art events in an intimate setting.
The great outdoors, arts, and solace unite in these towns, with something for every taste, like Woodstock, a hip destination for music lovers. And let's not forget the Long Island detour, with coastal towns like Greenport offering some of the most beautiful beaches near New York City and a rich maritime history.
Although the Finger Lakes region feels less crowded after the summer season, Ithaca is in prime school mode. Falltime peepers rejoice in the leafy Westfield, home to waterfalls, a lighthouse, and Portage Pie for a slice after a foliage drive along the Seaway Trail. With something for everyone, plan a zen-day trip, a weekend getaway, or a holiday vacation.
