The Rockefeller family estate at Kykuit, in nearby Pocantico Hills, is open by guided tour. The property includes terraced gardens, Hudson River views, and an impressive collection of modern and classical art. Photo: Jake Carter

Tarrytown and neighboring Sleepy Hollow make for one of the Hudson Valley’s most accessible escapes – less than an hour-long, scenic Metro-North ride from Grand Central. The villages sit side by side on the river, tied together by their literary history as the home of Washington Irving and his iconic Legend of Sleepy Hollow.

Each October, the area transforms into one of New York’s most spirited destinations, with haunted hayrides, lantern-lit cemetery tours, pumpkin displays, and festivals that draw visitors from all over. Outside the fall season, Tarrytown and Sleepy Hollow remain year-round draws with historic estates, Hudson River views, and a growing restaurant scene.

Through September and October, Sleepy Hollow Cemetery offers guided walking tours that let visitors wander among historic graves and towering trees. Daytime tours highlight the autumn landscape, while evening lantern-lit tours cast the grounds in an eerie glow. Photo: Hannah Crisafulli

The draw to Tarrytown and Sleepy Hollow starts with history. Anchoring downtown, the Tarrytown Music Hall remains Westchester’s oldest theater, with a full calendar of concerts and film screenings. Along the river, landmark estates tell the story of the Hudson Valley’s Gilded Age: Washington Irving’s Sunnyside, the Gothic Revival masterpiece of Lyndhurst Mansion, and the grand Rockefeller Estate at Kykuit. Each is open seasonally for guided tours that highlight architecture, art, and gardens.

Equally compelling are the town’s atmospheric haunts. The Sleepy Hollow Cemetery and Old Dutch Church, set among rolling hills and ancient trees, are especially evocative in autumn. Lantern-lit tours, historic reenactments, and the annual Great Jack O’Lantern Blaze make October the busiest time of year.

For a quieter escape, outdoor options abound. Check sources like AllTrails for wooded trails and preserves just minutes from Main Street. The landscaped lawns of Lyndhurst make a perfect place to roam after a mansion tour, while the Mario Cuomo Bridge Path provides walkers and cyclists with sweeping views of the Hudson and Manhattan skyline. On Saturdays, the TaSH Farmers Market at Patriot’s Park brings local produce and makers to the historic village green.

On Main Street, Tarrytown offers an eclectic collection of shops. Trilogy Consignment is lightly witchy and stocked with a rotating mix of vintage and modern clothing, with a showroom that highlights truly elevated pieces. Nearby, ONA features a seasonally changing inventory of fair-trade goods, decor, all thoughtfully sourced from ethical creators. Flying Fingers Yarn Shop feels especially cozy, its floor-to-ceiling shelves brimming with unique yarns, buttons, and fiber arts materials that invite hands-on exploration. For book lovers, Transom Bookshop is a classic indie gem that stocks bestsellers, collectible classics, and more.

Along Main Street in Tarrytown, shops, cafés, and bars are close at hand, making it easy to explore the town. Photo: Hannah Crisafulli

Begin the day at Muddy Water, where a throwback coffee shop layout and classic espresso drinks offer a familiar, comforting feel. Down the block, The Bakehouse of Tarrytown, tucked into the historic train station, turns out excellent breads, sandwiches, and pastries in a photogenic setting.

For lunch, The Taco Project delivers consistently good tacos in a colorful, casual space, while Bibille offers classic Korean food in an unfussy setting. Mint Premium Foods — recognized by the Michelin Guide — serves Mediterranean plates in a quirky market-restaurant hybrid that feels more Brooklyn than suburb. A short hop south in Irvington, MP Taverna brings chef-driven Greek cooking with a contemporary edge, another Michelin-noted spot that’s earned a devoted following.

In the evening, Goosefeather is the standout: chef Dale Talde’s modern Cantonese restaurant inside the historic Tarrytown House Estate. The menu is inventive, the cocktails are sharp, and the setting, a 19th-century mansion with layered interiors and leafy grounds, makes it a destination on its own. For a taste of Spain, Basque delivers authentic tapas designed to pair beautifully with wine.

For a more casual night, Horsefeathers is a beloved pub rumored to be haunted, with shelves of books, an encyclopedic burger list, and decades of local lore. Setback Inn, neon-lit and a little rough around the edges, preserves a bit of old Tarrytown grit in a town that otherwise leans polished. Last but not least, Bridge View Tavern stays reliable for a pint and sunset views over the Hudson before catching the train.

The Metro-North Hudson Line follows the river north from Manhattan, passing tree-lined shores, bridges, and small towns along the way. Two stations serve the area: Tarrytown Station, about 53 minutes from Grand Central, is a five-minute walk from the shops and restaurants along Main Street and Broadway, while Philipse Manor Station in Sleepy Hollow takes 56 minutes and sits within walking distance of the Sleepy Hollow Cemetery and Kykuit, the Rockefeller Estate. These two stops give visitors the choice to begin their day immersed in history or wandering through the town center’s curated shops and cafes.