New York

10 Best Places for Weekend Trips From Hempstead, NY

12 Jun 2026Updated last time

Weekend Getaway Itinerary Overview from Hempstead, NY

Embark on a memorable journey with our curated selection of the top 10 weekend destinations near Hempstead, NY. Start your adventure by unwinding on the picturesque shores of Montauk, exploring the glamorous villages and stunning beaches of The Hamptons, or reveling in the laid-back charm of Fire Island's unique, car-free environment. Nature lovers can hike scenic trails and enjoy panoramic vistas at Bear Mountain State Park or discover the immersive art installations at Storm King Art Center. Dive into culture and history with a visit to Philadelphia, PA, known for its iconic landmarks and vibrant food scene, or stroll through the cultural treasures of New Haven, CT, home to Yale University. Artistic souls will be captivated by Beacon’s galleries and Dia:Beacon, while Hudson, NY invites you with its antique shops and historic streets. Conclude your trip in Mystic, CT, where maritime history and aquarium adventures await. Each location offers a unique experience, perfect for unwinding and making unforgettable memories close to home.

Recommended Activities

  • 1

    Montauk

    Montauk offers beautiful beaches, scenic lighthouse views, fresh seafood, and a relaxed coastal atmosphere perfect for a peaceful weekend retreat.
    Montauk
    Montauk
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    Montauk
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    Montauk
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    Montauk
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  • 2

    The Hamptons

    The Hamptons are famous for charming villages, stunning beaches, upscale restaurants, and a vibrant arts scene, making it ideal for a luxurious and memorable getaway.
    The Hamptons
    The Hamptons
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    The Hamptons
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    The Hamptons
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    The Hamptons
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  • 3

    Fire Island

    Fire Island is known for its pristine sandy beaches, unique car-free communities, picturesque boardwalks, and opportunities for outdoor activities like biking and wildlife watching.
    Fire Island
    Fire Island
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  • 4

    Bear Mountain State Park

    Bear Mountain State Park is ideal for hiking, picnicking, and enjoying breathtaking views of the Hudson River, with attractions like a zoo, lake, and historic inn for a perfect nature escape.
    Bear Mountain State Park
    Bear Mountain State Park
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    Bear Mountain State Park
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    Bear Mountain State Park
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    Bear Mountain State Park
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    Bear Mountain State Park
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    Bear Mountain State Park
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    Bear Mountain State Park
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    Bear Mountain State Park
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  • 5

    Philadelphia, PA

    Philadelphia offers rich American history, famous landmarks like the Liberty Bell and Independence Hall, renowned museums, and vibrant food markets for a culturally enriching weekend.
    Philadelphia, PA
    Philadelphia, PA
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    Philadelphia, PA
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    Philadelphia, PA
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    Philadelphia, PA
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  • 6

    New Haven, CT

    New Haven is home to Yale University, with beautiful campus architecture, world-class museums, lively eateries, and a burgeoning arts and music scene, making it a diverse urban getaway.
    New Haven, CT
    New Haven, CT
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    New Haven, CT
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    New Haven, CT
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  • 7

    Beacon, NY

    Beacon is known for its vibrant arts community, the renowned Dia:Beacon contemporary art museum, scenic hiking trails, and charming Main Street filled with shops, galleries, and cafes.
    Beacon, NY
    Beacon, NY
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    Beacon, NY
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    Beacon, NY
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  • 8

    Storm King Art Center

    Storm King Art Center offers a unique outdoor experience with massive contemporary sculptures set in a sprawling landscape, perfect for art lovers and nature enthusiasts alike.
    Storm King Art Center
    Storm King Art Center
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    Storm King Art Center
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    Storm King Art Center
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    Storm King Art Center
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  • 9

    Hudson, NY

    Hudson features a lively downtown with antique shops, farm-to-table restaurants, historic architecture, and a thriving arts and music scene, making it a trendy and relaxing destination.
    Hudson, NY
    Hudson, NY
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    Hudson, NY
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    Hudson, NY
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    Hudson, NY
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  • 10

    Mystic, CT

    Mystic is famous for its historic seaport, charming downtown, beautiful waterfront, engaging maritime museums, and family-friendly attractions like the Mystic Aquarium, making it an ideal spot for both relaxation and exploration.
    Mystic, CT
    Mystic, CT
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    Mystic, CT
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    Mystic, CT
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    Mystic, CT
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    Mystic, CT
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Restaurants

  • Picture for The Lobster Roll (LUNCH)

    The Lobster Roll (LUNCH)

    1980 Montauk Hwy, Amagansett, NY 11930, USA
    This iconic roadside eatery in Amagansett serves up classic lobster rolls and retro vibes, making it a must-stop for a genuine Hamptons experience.
    4.5
    $$$$
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    • Picture for Mystic Pizza, Mystic, CT

      Mystic Pizza, Mystic, CT

      56 W Main St, Mystic, CT 06355, United States
      Made famous by the 1988 movie, this pizzeria in Mystic, CT offers delicious pies and a nostalgic atmosphere for movie buffs and foodies alike.
      4.4
      $$$$
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      • Picture for The Pandorica

        The Pandorica

        165 Main St, Beacon, NY 12508, USA
        A Doctor Who-themed eatery in Beacon, NY with a quirky menu and décor, perfect for sci-fi fans seeking a unique and immersive dining experience.
        4.4
        $$$$
        Google Maps
        • Picture for Terrain Garden Café

          Terrain Garden Café

          561 Post Rd E, Westport, CT 06880, USA
          Located in Westport, CT, this charming café is set within a garden and lifestyle shop, offering farm-to-table dishes in a truly enchanting setting.
          4.4
          $$$$
          Google Maps
          • Picture for The Cave Mountain Brewing Company

            The Cave Mountain Brewing Company

            5351 Main St, Windham, NY 12496, USA
            Set in the Catskills near Hudson, NY, this brewery offers creative pub fare and craft beers in a cozy, rustic hideaway that feels worlds away from the city.
            4.6
            Google Maps

            Hotels

            • The Surf Lodge

              183 Edgemere St, Montauk, NY 11954, USA

              5.0
              An iconic Montauk hotel known for its laid-back beach atmosphere, live music, and stylish bohemian décor, perfect for a memorable coastal stay.

            • Winvian Farm

              155 Alain White Rd, Morris, CT 06763, United States

              4.6
              Located in the Litchfield Hills, CT, this luxury resort offers themed cottages including a treehouse and a restored helicopter suite, making each stay unique and adventurous.

              • The Dan'l Webster Inn & Spa

                149 Main St Suite #1, Sandwich, MA 02563, United States

                4.4
                A historic inn in Sandwich, MA with uniquely decorated rooms, beautiful gardens, and a blend of colonial charm and modern luxury amenities.

                • The Roundhouse

                  2 E Main St, Beacon, NY 12508, United States

                  4.1
                  A boutique hotel in Beacon, NY with rooms overlooking waterfalls and modern, industrial-chic design, offering a romantic and scenic atmosphere.

                • The Inn at Stony Creek

                  34 Spanktown Rd, Warwick, NY 10990, USA

                  4.9
                  A quaint B&B in Warwick, NY surrounded by nature, featuring themed rooms and personalized touches for an intimate, countryside escape.

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