9 Picturesque Towns in New York for a Weekend Retreat in 2024
Despite the state's famous attractions—not just the Big Apple—New York City is largely a concrete jungle, making one yearn for a retreat. Offering to exchange the unending city pace for the undulating natural serenity, these nine small towns are idyllic for a weekend retreat in 2024. The serene atmosphere is enhanced by their unique natural surroundings, from the Adirondacks in Lake George and Saranac to Trumansburg of the Finger Lakes.
Chatham
Walking through Chatham Downtown is like traveling through Americana, albeit an eclectic mix of comfort stays and fine-dining restaurants. From Our Daily Bread Deli for a java companion to kickstart your morning to the events and a Ferris wheel at the Columbia County Fair Grounds, Chatham has lots to experience. See what musical is playing nearby at Mac-Haydn Theatre, an intimate, 350-seat theater presenting Broadway revivals and kids' shows. Home to small-town hotspots like Lagonia's Bistro, Crow Cottage, a gift shop, and Chatham Brewing, the local favorite watering hole, which is a stroll away from the Stony Kill.
The proudest feature of downtown Chatham is the Main's clock tower from 1872, which is in working order for a selfie or a short video backdrop. Also on the Main, Bimi's Cheese Shop is unmissable for a fine selection of local cheeses, plus coffee and a bakery to fuel your ventures. Once you feel winded, the over-40-year-old Chatham Book Store complements a shopping spree, offering a lovely space for leisurely browsing before Chatham Grill for dinner. Smith's Pond to the west and Borden's, a hiking area just east, offer the outdoors from the doorstep of your lovely stay, like Art Park, a small, stylish inn with a hot tub.
Freeport
Exuding a relaxing vibe, Freeport is a charming town at the base of Long Island, steeped in watery views and town greens. Its South Shore Blueway Trail attracts non-motorized boaters to sail along a recreational, environmentally friendly waterway in between parks, historic sites, and nature areas. You can reroute to another stream or stop for a greenway bike ride or a hike that connects to more preserves, parks, wetlands, and islands within the South Shore Estuary Reserve. Hibiscus on the Mile is a must-hit for seafood lovers, while Coral House is a multi-menu American restaurant in a beautiful building next to Milburn Creek Park. Nearby, Baldwin Bowl & Lounge—Ultra Lanes is an energetic spot for bowling, with food and big screens, plus a lounge.
The 2.693-acre Waterfront Park offers a playground, a large picnic area with two pavilions, and waterfront walking paths with a fishing area and a scenic gazebo overlooking Little Swift Creek and Baldwin Bay. Its astronomy program is free to join on Tuesday evenings in July and August. You don't have to leave the bayfront for dinner on the cozy outdoor patio at Sonny's Canal House, or go for the breezy and informal Bracco's Clam & Oyster Bar, serving raw and cooked seafood bites with tropical drinks. From the Freeport Inn and Marina, you have easy access to the 171-acre waterfront park and preserve, Cow Meadow Park, with a marina, fishing, sports fields, and hiking trails. In the north, Martin Luther King, Jr. Park offers two free outdoor swimming pools for families.
High Falls
Nestled up against Rondout Creek, High Falls is just a short trip from NYC, perfect for a weekend jaunt. Across the Lucas Turnpike from the larger town of Stone Ridge, High Falls offers an enviable laidback feel and mix of natural features. The small Ulster County hamlet, once known for its canal and named after the 150-foot eponymous waterfall in the Hudson Valley, is a premier town in the Hudson Valley. High Falls attracts antiquers and dining enthusiasts with homey places like Ollie's Pizza. Sky Lake Lodge is a popular stay in town as well. Stop by D&H Canal Historical, a museum bordering the former waterway and D&H Canal Roebling Bridge.
A trip to High Falls is incomplete without a hike to the waterfall, complete with a lovely picnic in the mist. South of town, Table Rocks attract hikers with its unique features, which allow them to scramble around and enjoy a one-on-one photo shoot with nature. The town also features tiny galleries, the Well of Souls, and the opportunity to pick up a pretty bouquet for someone special at the cute Green Cottage. The tasteful Wired Gallery showcases area artists, while the Spy Social Eatery and Bar is a destination in itself, offering New American fare with veggie picks and wine galore in farmhouse digs and a screened porch. Stop next door at the High Falls flea market, popular among visitors to browse for a special memory of the town.
Lake George
Home to under 3,500, Lake George is a small town with a huge personality on a serene namesake lake. Displaying a true Adirondacks spirit through heritage and natural beauty, there's more than a weekend getaway worth of relaxation and intrigue. Steeped in Colonial and Revolutionary War history, the Fort William Henry Museum reminisces on its strategic importance during the French and Indian conflict. Many enjoy the tour around the waterfront fort, including pretty lake views during live demonstrations of musket and cannon firing. The nearby Million Dollar Beach is open from late May through early September and is free to the public. It includes showers, lifeguards, picnic areas, and a boat launch—just pay for parking. The couples enjoy a memorable cruise on a historic vessel with Lake George Steamboat Company.
Prospect Mountain Highway offers lovely overlooks on a drive, including the lake in a colorful frame of fall. Enjoy leaf-peeping along Prospect Mountain Hiking Trail or a snowshoeing adventure in the winter. Barnsider Smokehouse BBQ is a hiker's favorite for an array of smoked meats plus classic American comfort fare, sides, and beer on an ample patio. You'll be tripping over accommodation options here, but Admiral Motel is a top-rated budget stay by the water. The waterfront Shepard Park delights families from the doorstep, with beach access, a playground, and an amphitheater for summer concerts. After an adventure with Kayak Lake George, grab a drink at the cabin-like Garrison on a patio with live music. No family visit is complete without the pirate-themed 18-hole minigolf among waterfalls and caves.
Montauk
Marking the easternmost part of Long Island, Montauk is a world-renowned destination with a laidback vibe and nature advantage in between many beaches and pristine coastal parks. From boating to paddling and fishing, the proud Montauk Point Lighthouse is perched at the very tip. Built in 1796, it is the nation's fourth-oldest and the oldest active lighthouse in New York. Montauk County Park offers a sprawling waterfront with a pond and horseback riding trails, plus the site of the first US cattle ranch. Next to Lake Montauk, the large Ditch Plains Beach is popular among watersport lovers and families alike for surfing, swimming, and sunbathing along the sands in scenic views. You don't have to go far for a bite—just a hop to Duryea's Montauk, a unique self-serve waterfront eatery.
Montauk Downs State Park offers a pool, tennis courts, and an 18-hole golf course designed by Robert Trent Jones, Sr. For those visiting in winter or looking for cultural experiences or a relaxing stay, Montauk boasts some pretty options, like Ocean Vista Resort, plus fine dining through excellent restaurants. Navy Beach Restaurant serves simple seafood and burgers with outdoor seats and a nautical interior, while Harvest on Fort Pond has the bygone era feel, serving platters of Tuscan-style Italian cooking, family-style, waterfront. For serenity, escape to the nearby white-sanded Kirk Park Beach. Between here and the next town along the peninsula sprawls Hither Woods Preserve.
Saranac Lake
Follow the beautiful stretch of road through the Adirondacks High Peaks region, past Keene and the touristy Lake Placid. Welcome to Saranac Lake, a real nature lover’s paradise, feeling secluded against the edge of McKenzie Mountain Wilderness. Tangled amid forest trails and dirt roads, Saranac Lake exudes authentic small-town Adirondack vibes, blending adventure with a tagline, “decidedly different," into four seasons of outdoor attractions. This Upstate destination offers a winter wonderland under the snowy conditions, with access to the Whiteface Mountain's signature skiing slopes. Stop by the French-inspired Blue Moon Café and stay along Lake Flower at Sara Placid Inn & Suites.
The springtime rivers are full-flowing, and ponds filled with snowmelt transform the surrounding scenery into lush landscapes. In the summer, enjoy the lake for paddling and swimming, plus adventurous hikes like Baker Mountain Trailhead east to Mount Baker Peak. Spring through fall hiking is as bountiful and uncrowded as the vast Adirondacks landscapes. Having dubbed itself "The Adirondacks' Coolest Place," there is a slew of proof amid stunning mountains. From Robert Louis Stevenson Cottage, buried in the wilderness, to the antiquated Adirondack Carousel with carved horses and historic themes downtown, Saranac Lake is sure to impress, alongside Red Fox, which offers delicious dining away from the crowds.
Saugerties
Nestled between the Hudson River and the Catskill Mountains, this Mid Hudson Valley town is one of New York’s coolest, with Overlook Mountain views to the west. Its small downtown area bathes in natural beauty, history, and small-town charm through antique shops, cafés, and art galleries. Calling for a relaxing afternoon stroll, the lovely commercial district stretches along the easily walkable Main and Partition streets. Opus 40, an environmental sculpture and museum, was created by sculptor and quarryman Harvey Fite. Attracting culture fans and the curious from around the nation, this series of dry-stone ramps, pedestals, and platforms sprawls over 6.5 acres of bluestone. Saugerties is also known for its historic Saugerties Lighthouse.
Dating back to 1869, the lighthouse at the Esopus Creek intersection doubles as a luxurious bed and breakfast with two rooms for a memorable or romantic overnight stay. Guests have access to the top of the tower for stunning views of the river and the surrounding landscapes. Nearby, the gentle half-mile winding trail through wetlands presents birding opportunities. From the Indian Head Wilderness to the steep and rocky Devil's Trail ascending five peaks, with rock formations, waterfalls, and views of the Catskills, Saugerties can satisfy any outdoor craving. For an epic weekend getaway, take a stroll through Falling Waters Preserve and Esopus Creek Conservatory, plus a stop at the Catskill Animal Sanctuary.
Sleepy Hollow
Just 25 miles north of the Big Apple in Westchester County, visit the main inspiration for Washington Irving's “The Legend of Sleepy Hollow.” Sleepy Hollow, a real-world Halloween-themed village within the town of Mount Pleasant, is one of New York's most picturesque. Complete with a rustic lighthouse circa the 1880s and historic residences like Philipsburg Manor, Sleepy Hollow offers a fun and laidback feel year-round within scenic natural surroundings. Take a stroll through the serene Sleepy Hollow Cemetery, the final resting place of many real-life characters from the tale. For dinner, Bridge View Tavern welcomes patrons with an array of microbrews and pub grub, while Tarrytown House Estate on The Hudson may set you back but is worth the pretty buck.
Boasting the pet-friendly Scenic Hudson Riverwalk, a beautiful stroll or setting for a picnic, enjoy the mountain views across the river, the Tappan Zee bridge, and the lighthouse, particularly at sunset. Just south, Lyndhurst Mansion is a stunning 19th-century Gothic Revival mansion on a 67-acre estate with self-guided audio tours. Stop by the historic Kykuit, the Rockefeller estate, a landmark with tours of a 40-room home, gardens, and art collection, plus panoramic views. The next-door Washington Irving's Sunnyside is the famed author's charming riverfront house, complete with costumed guides and scenic gardens. Rockefeller State Park Preserve features a system of historic carriage roads through woodlands, meadows, and fields. Oh, and this town just celebrated its 150th birthday!
Trumansburg
Due to the misspelling of the founder's name, Abner Treman, welcome to Trumansburg, which actually does remind you of The Truman Show thanks to its idyllic feel. With Trumansburg Creek through the heart and Taughannock Creek just south, the locals enjoy access to creekside strolls. Minutes from the long Cayuga Lake's western shore, make a quick drive to the lakefront Frontenac Point Vineyard & Estate Winery, perfect for the harvest season's bounty of tastings and views. This Finger Lakes town boasts a fantastic highlight, the Taughannock Falls. Play a round at Trumansburg Golf Course and take the 3/4-mile Gorge Trail to the 215-foot Taughannock Falls, the tallest waterfall east of the Rockies.
Meanwhile, the 16 Elm Heritage Hotel is a top-rated stay, and Hazelnut Kitchen serves farm-to-table fare, like chicken schnitzel, complete with a wine list. The next-door Trumansburg Main Street Market is the organic hotspot in town. The Spa at Gothic Eves offers relaxation after a hike, or choose from the many wineries in the area, like Idiot Brothers Cider. More into suds? How about imbibing local culture at Garrett's microbrewery? Next to the old, columned Ulysses Philomathic Library, stop by Ulysses Historical Society and don't miss the unique Salmon Pottery Gallery & Studio for viewing or a class to make pottery. Atlas Bowl is a popular bowling alley, while Falls Restaurant & Catering serves American fare away from the downtown action.
Yearning for a memorable weekend of tranquility with adventures at your fingertips? Saugerties offers a vibrant mix of attractions for an epic weekend getaway, including Opus 40 and the historic Saugerties Lighthouse, which doubles as a romantic B&B. Freeport boasts the South Shore Blueway Trail, Saranac Lake offers access to Whiteface Mountain's signature skiing slopes, and Lake George is a leaf-peeping paradise along Prospect Mountain Hiking Trail. Each as different as the sprawling Empire allows, the one-of-a-kind attractions cater to different interests.
