A Village Hidden In New York's Hudson Valley Is A Cute Riverside Gem With Hillside Views And Quaint Shops

Located only an hour by train from Midtown Manhattan, this quiet town is a hidden gem filled with cafes, shops, and charm in the middle of the Hudson Valley. Ossining sits on the eastern shore of the Hudson River, sharing the area with similarly small, idyllic villages, including Sleepy Hollow, a cozy town that has plenty of charm and a paranormal legacy. In addition to water views, Ossining's historic downtown center offers a mix of nature, history, and independent shops to enjoy.

Built into the hills of the Hudson Valley, you'll get great views of the river from the town and its surrounding parks. Hiking is a great way to take in the local scenery, whether you try the Croton Aqueduct Trail or head to Teatown. If staying in town until sunset, finding a restaurant with outdoor seating or a view is highly recommended by past visitors (3 Westerly and The Boathouse are two solid options for dinner near the river) or, if you aren't feeling a meal, you can always plant yourself near the river at one of Ossining's many parks.

Ossining is easily accessible from the city and nearby suburbs by car. Public street parking, as well as parking at hiking trails, is readily available. It is possible to walk around town, but you may want the freedom of a car to travel around, particularly if you plan to stop elsewhere in the Hudson Valley or stay at a nearby hotel (maybe even one that claims to be America's oldest inn).

Two major activities in any small town in the Hudson Valley are strolling and exploring local cafes and shops, and Ossining delivers on both. On Main Street, Ossining's bustling main drag, you'll find home good stores, boutiques, a bookstore, and a record store. No matter what time of day, you'll find great options for food or drinks in town — some on Main Street and others a short drive away. This includes delectable breakfast spots like First Village Coffee and The Tasty Table as well as casual lunch fare at Brothers Fish & Chips or bars like Here Coffee and Beer and Sing Sing Kill Brewery.

A little on the outskirts of town but not to be missed is Teatown, Ossining's 1,000-acre nature reserve and education center. Trails are open from sunrise to sunset here every day, but the reserve also hosts specialty hiking groups — like its Women Take to the Trails and Sunset Series. Some hiking series are free, and others may require a ticket. However, prices are low for non-members at only around $10. The park also has attractions like Wildflower Island (which is only accessible via tour) and an educational sensory garden. When visiting Teatown, parking tags are required from 9 a.m. to 5 p.m. and cost $7 per car for non-members.

Originally named the Village of Sing Sing when it was founded in 1813, Ossining officially became the town as it's known today in 1901. The 2023 film "Sing Sing" depicts the famous correctional facility in Ossining, which remains a major part of the town's history. In Ossining, you'll find the Sing Sing Prison Museum, which in 2025, will be commemorating its 200-year-long history.

Historic walking tours of Ossining are a popular way to explore the town. The Village of Ossining has an official self-guided walking tour, with PDF versions available to download to your phone online in addition to hard copies at the Ossining Public Library, Village Hall, and Joseph Caputo Community Center. In addition to providing a walking route, the tour PDF will take you through the historic buildings and markers in town and will explain what they used to be, when they were built, and the significance they may continue to hold. Some spots you can expect to see include the Ossining Railroad Station, The Crescent (modern day Main Street), Churches, and more. Continue your journey afterward by visiting the village of Cold Spring, which is located only a 30-minute drive from Ossining and is a charming and walkable New York village that is brimming with cafes and shops.