Road.Travel Road.Travel
    7 Activities

    Winding Through Westchester: Markets, Museums, and Modern Art

    Winding Through Westchester: Markets, Museums, and Modern Art
    Starts from

    New York

    Transportation

    By Car

    Guidance

    Self-Guided

    Activities

    7

    Duration

    11 hours

    Length

    41 mi

    Guide details

    Starts from

    New York

    Transportation

    By Car

    Guidance

    Self-Guided

    Duration

    11 hours

    Length

    41 mi

    History and Culture🎁 Weekly giveaways
    Map preview
    Kristan Schiller

    Kristan Schiller

    Traveller

    • Stock up on artisanal cheese at farmer's markets.
    • Explore a community-run prison museum.
    • Visit a contemporary art gallery on the banks of the Hudson River.
    Stock up on artisinal cheese and fresh jams at farmer's markets and farmstands straddling the scenic Hudson River. Pass through Ossining, New York, the fictional home of Don and Betty Draper in the hit TV series Mad Men and the real-life home of Sing Sing, one of America's most notorious prisons. You can even visit a temporary Sing Sing Museum at the Ossining Community Center. Feast on authentic Caribbean fare in an excellent Jamaican restaurant, view contemporary art in a reimagined printing factory, and wind down your day in an upscale hotel on the banks of Fishkill Creek in Dutchess County.

    Categories

    Stock up on artisinal cheese and fresh jams at farmer's markets and farmstands straddling the scenic Hudson River. Pass through Ossining, New York, the fictional home of Don and Betty Draper in the hit TV series Mad Men and the real-life home of Sing Sing, one of America's most notorious prisons. You can even visit a temporary Sing Sing Museum at the Ossining Community Center. Feast on authentic Caribbean fare in an excellent Jamaican restaurant, view contemporary art in a reimagined printing factory, and wind down your day in an upscale hotel on the banks of Fishkill Creek in Dutchess County.
    Kristan Schiller

    Kristan Schiller

    Traveller

    • Stock up on artisanal cheese at farmer's markets.
    • Explore a community-run prison museum.
    • Visit a contemporary art gallery on the banks of the Hudson River.

    Day Itinerary

    7 Activities
    Map preview

    Day 1

    41 mi0.3 mi

    Discover Farmer's Markets, Caribbean Fare and Contemporary Art

    Peruse one of Westchester County's best farmer's markets. Visit the community-run museum, dedicated to one of America's most notorious prisons. Enjoy Caribbean food, then view contemporary art in a reimagined printing factory in Beacon, New York.
    You will head north just east of the Hudson River for your scenic road trip through Westchester County. Prepare for a fun day of markets, museums, and modern art!
    The TaSH Farmers Market
    09:001 hr

    The TaSH Farmers Market

    Farmers Market
    Open Details
    The TaSH, Tarrytown & Sleepy Hollow Farmers Market, takes place in an outdoor park between Tarrytown and Sleepy Hollow, New York. Stock up on fresh produce and stop at one of the many stands for coffee and a bite of breakfast.
    If the market is closed, head to Main Street in Tarrytown and hit Coffee Labs Roasters for a scone and coffee, then visit the excellent shops including yarn shop Flying Fingers and toy store A Nu Toy Store.
    5.9 mi
    15 min
    10:1545 min

    Ossining Community Center

    Event Service
    Open Details
    Ossining, New York, is the fictional home of Don and Betty Draper from TV's popular Mad Men series, but also the real-life home of one of America's most famous maximum security prisons, Sing Sing.
    There's an interesting (and free) exhibit about the prison and its gruesome past attached to the Ossining Community Center with a wall of homemade weapons, a replica of the electric chair that was used there for decades, and a recreation of a Sing Sing cell block. A much larger Sing Sing museum is currently under development at the site of the now defunct 1824 cellblock, but until it's complete, this tiny display is a worthwhile stop.
    0.3 mi
    10 min
    Melita's Home
    11:3015 min

    Melita's Home

    Boutique
    Open Details
    Amble along Main Street and pop into Melita's Home, which carries everything from ceramics to women's clothing to furniture. Melita's is one of those "something for everyone" shops, and the owner is helpful and hospitable.
    0.1 mi
    5 min
    Cravin
    12:0045 min

    Cravin

    Restaurant
    Open Details
    Just a block from Melita's is Cravin' Jamaican Cuisine, where you can feast on a lunch of authentic jerk chicken with rice and beans, red snapper with peppers, or curry shrimp. The tasty cuisine and friendly atmosphere will put a smile on your face as you hop back on the road.
    Please be aware that if you intend to join the upcoming farm tour (check the schedule in advance), you may need to skip or expedite one of the activities planned in Ossining.
    9.6 mi
    25 min
    Hemlock Hill Farm
    13:1545 min

    Hemlock Hill Farm

    Farm
    Open Details
    The Hemlock Hill Farm & Market Store is a treasure trove of farm fresh meats, produce, and other goodies. You'll be greeted with genuine warmth and a welcoming atmosphere. The farm's commitment to providing access to local, organic, and farm-fresh products ensures that you can savor the flavors of the region. Peruse the shop, ask questions, and fill your market basket! In addition, tours of the farm can be booked online.
    24.5 mi
    50 min
    Dia Beacon
    15:002 hrs

    Dia Beacon

    Art Museum
    Open Details
    Here, at Dia Beacon, you'll find a former printing factory filled with contemporary art. Inside a giant 240,000-square-foot space with sawtooth skylights and hardwood floors, Dia displays the works of 25 minimalist and conceptual artists from Gerhard Richter to Donald Judd.
    1.6 mi
    5 min
    The Roundhouse
    17:302 hrs

    The Roundhouse

    Restaurant
    Open Details
    The Roundhouse, once a dye mill, is now a stylish hotel that has Beacon Falls as an after dinner view instead of an energy source. Here you may have dinner in a farm-to-table restaurant overlooking Fishkill Creek and settle in for the evening. After a delicious dinner, wander along Main Street in Beacon, New York, with its mix of cafés, galleries, and boutiques. Or feel free to save that idea for tomorrow morning!
    You may book a room in the hotel and enjoy the soothing sound of the Hudson River flowing by as you relax at the Roundhouse, your rustic retreat for the night, before heading back to Manhattan in the morning.
    Map preview
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