This Upstate New York Downtown Is Made For Strolling

Skaneateles, an idyllic town of 7,000 in the heart of the Finger Lakes region, sits at the northern end of Skaneateles Lake in Upstate New York, where the village’s downtown meets the water. With its lakefront parks flowing seamlessly into a compact historic core, Skaneateles is designed for wandering on foot. A stroll can begin at Clift Park and its long pier over the water, continue along Genesee Street past the Sherwood Inn and 19th-century storefronts, then slip down Jordan Street for boutiques, bakeries, and quiet corners. Green spaces like Thayer Park punctuate the walk, keeping the lake always within sight. If this rhythm appeals, read on for two more New York towns that offer similarly inviting streetscapes worth exploring next.

Clift Park and the Pier

The walking tour of town starts at Clift Park, which runs alongside the lake at the edge of downtown. Functioning as both a community gathering space and a stunning visual landmark, the park offers open lawns, benches facing the water, and a pier that extends straight into the lake for a wide view of the shoreline and surrounding hills, grounding the town’s relationship to the water. Spend time soaking it in and getting your bearings in the "Jewel of the Finger Lakes." When you're ready to explore, West Genesee Street sits just steps from the park, making a natural transition from the waterfront into the historic streets of downtown.

Genesee Street: The Spine of Skaneateles

Turn right onto West Genesee Street and head east toward town. Also known as US Route 20, this thoroughfare serves as the main axis of the village, lined with two and three-storey buildings that date mostly back to the 19th century. Many retain original brick or stone facades, with upper-floor windows that reflect the region's early days and generous sidewalks that make it easy to walk at a relaxed pace while moving between shops, bookstores, cafes, and galleries.

Along this stretch, you’ll pass the stately Sherwood Inn, an enduring legacy founded in 1807 as a stagecoach tavern, long serving as a social and hospitality hub in Skaneateles. Right next door is the Hannum House, a restored mid-19th-century residence that was home to one of the town's early leaders and entrepreneurs, Spencer Hannum, but now operates as a boutique inn with a handful of luxury guest suites. As downtown Skaneateles stretches only a few blocks, everything feels within reach. You’re never more than a few minutes from the lake or quieter residential streets just behind the commercial row.

Stepping Off the Main Drag

Jordan Street, which runs perpendicular to Genesee, reveals older homes, smaller businesses, and quieter sidewalks that juxtapose the activity of the main street. At the corner of Jordan and Genesee Streets stands the Seitz Building, a century-old structure now home to luxury condos. Its facade blends classic brickwork with warm, local timber accents, a true Skaneateles landmark. Jordan Street is a retail street filled with independent boutiques worth exploring. Whether browsing clothing and jewelry at Emma + James or leather goods and accessories at The Local Branch, visitors can combine their historic building tour with a bit of shopping and casual dining.

Those looking for a snack can step into Skaneateles Bakery for homestyle sandwiches, coffee, and donuts. These streets show how compact the village really is. You can step away from Genesee Street for a few minutes, then return without losing your sense of orientation. The grid is simple, and views of the lake can serve as a guide back to the main thoroughfare.

Thayer Park and the Eastern End of Downtown

Thayer Park is another peaceful green space in the heart of the village. The park was donated to the community by the family of Joel Thayer, former postmaster, businessman, and prominent resident. Thayer Park sits across from the historic Thayer House at 77 East Genesee Street, a home first built in 1829 and later remodeled during Thayer’s ownership. In July, Thayer Park hosts the annual Antique Boat Show, in which history buffs and nautical enthusiasts flood the town for demonstrations, a boat parade, and plenty of family-friendly activities. This section of the walk feels slightly quieter than the light bustle of the western end near Clift Park. From here, you can walk along the lake and its sturdy seawall, pause at the end of the water on one of the benches, then return to the sidewalk to retrace your steps west.

Shops, Galleries, and Everyday Stops Along the Way

Strolling back toward the centre of town, Genesee Street offers plenty of reasons to stop, with independent shops and eateries closely clustered together. For a caffeine fix and sweet treats, stop by Vermont Green Mountain Specialty Co., known for its wide selection of gourmet chocolates, or enjoy fusion seafood dishes with views of Skaneateles Lake at the Blue Water Grill. Just a short turn from Genesee Street onto Fennell Street, visitors can find Skaneateles Artisans housed in the Old Stone Mill. The gallery showcases work across many styles and media, created by over 90 artists from the Finger Lakes and New England regions.

From Fennell Street, Kelley Street links back to Hannum, where you will find the Skaneateles Historical Society Museum, housed in the Old Creamery, circa 1899. With collections that include custom and antique boats, photos, artifacts, and stories that provide context to the streets and sights of historic Skaneatles.

Two Other New York Downtowns With a Similar Look & Feel

Visitors who are drawn to Skaneateles' well-preserved streets and compact downtown are in luck, as there are a couple of other New York towns well worth exploring. Hudson’s downtown is centered on Warren Street, lined with a long stretch of Federal and Greek Revival buildings. The street feels wider and more urban than Skaneateles, but it shares the same focus on historic character and walkability. Like Skaneateles, Hudson is best enjoyed at a slow pace, especially if you love the mix of rural landscapes and city culture. The shops are an art lover and antique collector's dream, with galleries and vintage boutiques galore, while an eclectic mix of dining options includes Malaysian, Mexican, handcrafted sourdough pizza, and plenty of cafes and sweet shops along the way.

Cazenovia also shares Skaneateles’s combination of a lakefront setting and an accessible downtown. Although its commercial buildings are smaller in scale, they’re still similarly rooted in 19th-century design. Lorenzo State Historic Site is a historic mansion built in 1807 that offers tours and a glimpse of Central New York's early elite, while Lakeland Park is home to a boat launch, a small pier, and a sandy beach in the heart of town. Cazenovia’s close network of natural spaces, commercial buildings, and local shops makes strolling the perfect way to explore.

Discovering Skaneateles On Foot

To stroll around Skaneateles is to understand the town’s rich history, culture, and spirit. The village is arranged so that you can move from the lake at Clift Park, along the length of Genesee Street, and through quieter side streets, all in one unhurried loop. Along the way, there are historic buildings, shops, cafes, galleries, and parks, each inviting you to take your time and take it all in. Skaneateles asks very little of you. Start at the water, keep walking, and let the town set the pace.