Part small-town escape, part creative hideaway, Dobbs Ferry, New York is where city energy meets Hudson Valley calm.
Just a quick 35 minute Metro-North ride away from NYC, this charming village — recently spotlighted by Islands for its “scenic parks and historic charm” — feels like Brooklyn’s artsy cousin who moved upriver for a slower (and leafier) life.
Thanks to its leafy streets, golden foliage, and cozy cafés overlooking the Hudson River, it’s no wonder why this Westchester gem deemed the “Brooklyn-on-Hudson” is perfect to visit during the fall— it’s creative, scenic, and full of local character.
Part of Westchester County’s classic “River Towns,” goruping, Dobbs Ferry offers the perfect balance between small-town serenity and Hudson Valley vibrance.
Historic architecture, locally owned shops, and riverfront trails create a walkable charm that’s especially magical in autumn’s crisp light!
For starters, The Old Croton Aqueduct Trail runs right through the village, connecting it to neighboring Irvington and Hastings-on-Hudson — a scenic route that’s alaways lined with fiery foliage and historic stonework this time of the year.
Plus, for all you history buffs, Dobbs Ferry’s Revolutionary War roots run deep — the town played a key role in the final stages of the war, and the Dobbs Ferry Historical Society still preserves artifacts, documents, and stories from that time. (You can even visit it in-person and thumb through archives!)
Fall highlights & local events
Autumn in Dobbs Ferry is all about community, colors, and that unbeatable Hudson River backdrop!
Start with a leisurely walk or bike ride along the Old Croton Aqueduct Trail, where you’ll pass under canopies of changing leaves and historic homes.
Then head down to Waterfront Park, where sweeping river views meet the Palisades’ dramatic cliffs — especially stunning at sunset.
Each October, the town comes to life with seasonal fall events that are incredible for all ages!
While Ferry Festa (the town’s lively October street fair) already happened on October 5 and will return in 2026, there’s still plenty of seasonal fun happening this fall:
- Halloween Spectacular featuring “Hocus Pocus” – On Thursday, October 30, head to the Old Croton Aqueduct Keeper’s House (15 Walnut Street) for games, crafts, trick-or-treating, and an outdoor screening of the Halloween classic Hocus Pocus. Free and family-friendly, it’s a perfect mix of history and Halloween fun! More info
- Dobbs Ferry Halloween Happenings – Village Recreation – From October 23 – November 2, the Recreation Department hosts a week of themed events, including Downtown Window Painting, a Pet Parade, a Halloween Bash at Waterfront Park, and Downtown Trick or Treating and. Block Party on Halloween night! More info
Where to eat & drink in Dobbs Ferry
For a town with fewer than 12,000 residents, Dobbs Ferry’s dining scene punches well above its weight! It can’t properly earn it’s Brooklyn comparison without tasty food, and there’s surely no disappointing here.
- Half Moon – Right on the river, this spot serves Montauk seafood and oysters with unbeatable Hudson sunsets.
- The Cookery – A beloved Italian gastropub known for its nose-to-tail menu and cozy fall atmosphere.
- Harper’s – A modern bistro perfect for brunch or fireside dinner with a glass of wine in hand.
- Bellacosa Wine & Tapas Bar – Ideal for small plates and people-watching downtown.
- Rivertown General Store – A mix of home goods and coffee bar, this spot perfectly captures Dobbs Ferry’s artisanal charm.
How to make the most of your fall visit
Getting there is effortless — take Metro-North’s Hudson Line from Grand Central, and you’ll arrive in about 35 minutes. No car, no problem!
If you’re expanding your Dobbs Ferry fall getaway into a full Hudson Valley Halloween adventure, late October 2025 is packed with nearby festivals, haunted experiences, and parades offering cinematic autumn vibes—all easily reachable within 15–45 minutes of Dobbs Ferry.
Legendary Halloween & fall side quests to add to your Dobbs Ferry visit
- The Great Jack O’Lantern Blaze (Croton-on-Hudson) – Running through November 16, 2025, over 7,000 hand-carved pumpkins illuminate the historic Van Cortlandt Manor grounds in a synced light and music display. A 20-minute drive north of Dobbs Ferry, it’s perfect for families or date nights.
- Halloween in Sleepy Hollow & Tarrytown – On October 25, the Tarrytown Halloween Parade steps off at 5 pm from Patriots Park, featuring floats, live music, and outdoor dining along Main Street. Sleepy Hollow offers haunted hayrides, cemetery tours, and live performances of Irving’s Legend inside the Old Dutch Church. Bonus highlights: Sleepy Hollow Cemetery Night Tours, Twilight Village Night Market, and Hulda’s Night at Rockefeller State Park.
- Scared by the Sound – About 35 minutes from Dobbs Ferry in nearby Rye, this haunted house delivers movie-level scares, perfect for thrill seekers.
- Beacon’s Hocus Pocus Parade (Oct 25) – Family-friendly parade with a scavenger hunt and costumed marches along nearby Beacon’s Main Street.
- Hastings-on-Hudson Flea Market (Oct 26) – Antiques, local crafts, food, and live music just 10 minutes away.
- Irvington Historical Society Fall Benefit (Nov 9) – A cultural capstone with luncheon and film program celebrating Irvington’s legacies.