Blur Effect
Photo of AI-Magellan
2024-08-27
Edit Trip Edit
Bookmark TripSave

10 best places for weekend getaway from Bridgeport, CT

Best Weekend Getaways from Bridgeport, CT

Bridgeport, Connecticut, while being an industrious hub, offers ample opportunities for delightful weekend escapes. Whether you're seeking the serenity of nature, the charm of historic towns, or the thrill of outdoor adventures, you will find numerous destinations just a short drive away. From the maritime allure of Mystic Seaport and the cultural richness of New Haven to the natural beauty of Hammonasset Beach State Park, there is something for everyone to enjoy. Discover the stunning waterfalls at Kent Falls State Park, explore the picturesque landscapes of The Berkshires, and indulge in the coastal charm of Old Saybrook. Each of these destinations provides unique experiences, making them perfect for a memorable weekend getaway from Bridgeport.

Plan your dream trip for Free with AI
Create a personalized itinerary effortlessly with our AI-powered planner.
Upgrade BackgroundUpgrade Picture

Recommended Explorations

  • Trip Point Pin1

    Mystic Seaport

    Mystic Seaport offers a unique maritime experience with its well-preserved historic ships, interactive exhibits, and the chance to explore a recreated 19th-century seafaring village.
    Open Google Maps Button
  • New Haven is home to Yale University, offering rich cultural and historical landmarks, renowned museums, vibrant arts scenes, and diverse dining options.
    Open Google Maps Button
  • Trip Point Pin3

    Hammonasset Beach State Park

    Hammonasset Beach State Park provides two miles of beautiful shoreline, ideal for swimming, picnicking, hiking, and bird watching, making it the perfect location for a relaxing outdoor experience.
    Open Google Maps Button
  • Trip Point Pin4

    Bear Mountain State Park

    Bear Mountain State Park offers scenic hiking trails, breathtaking views from the Perkins Memorial Tower, a beautiful lake for boating, and a zoo, making it a perfect destination for outdoor enthusiasts.
    Open Google Maps Button
  • Trip Point Pin5

    Kent Falls State Park

    Kent Falls State Park is known for its stunning waterfall that cascades down 250 feet, surrounded by picturesque hiking trails and picnic areas, providing a serene natural escape.
    Open Google Maps Button
  • Trip Point Pin6

    The Berkshires

    The Berkshires are known for their picturesque landscapes, cultural attractions including Tanglewood and the Norman Rockwell Museum, charming small towns, and a variety of outdoor activities such as hiking, skiing, and zip-lining.
    Open Google Maps Button
  • Trip Point Pin7

    Old Saybrook

    Old Saybrook offers a mix of coastal charm and history with attractions like the picturesque Saybrook Point, the Katharine Hepburn Cultural Arts Center, and its inviting beaches and marinas.
    Open Google Maps Button
  • Newport is renowned for its stunning Gilded Age mansions, beautiful coastal scenery, historic sites such as Fort Adams, and the scenic Cliff Walk, making it a rich cultural and recreational destination.
    Open Google Maps Button
  • Trip Point Pin9

    Litchfield Hills

    Litchfield Hills captivates visitors with its rolling hills, scenic countryside, quaint villages, outdoor activities such as hiking and biking, and historic attractions like the Litchfield Historic District.
    Open Google Maps Button
  • Trip Point Pin10

    Mohonk Mountain House

    Mohonk Mountain House is a historic resort set in a stunning natural setting, offering a wide range of outdoor activities including hiking, boating, and golfing, along with luxurious spa services and exquisite dining options.
    Open Google Maps Button


Local Events & Happenings


Music for Your Journey


    Tasty Picks


    Stay Recommendations

    • Hotel Icon

      Winvian Farm

      Open Google Maps Button

      Winvian Farm

      A collection of whimsical, themed cottages set on a 113-acre farm, each offering a uniquely creative lodging experience.
      Open Google Maps Button
        Picture for Winvian Farm
      • Hotel Icon

        The Roundhouse at Beacon Falls

        Open Google Maps Button
        4.2

        The Roundhouse at Beacon Falls

        A boutique hotel housed in a restored 19th-century industrial building, featuring modern amenities and stunning river views.
        Open Google Maps Button
        4.2
        Picture for The Roundhouse at Beacon Falls
      • Hotel Icon

        The Library Hotel, New York, NY

        Open Google Maps Button
        4.6

        The Library Hotel, New York, NY

        A literary-themed boutique hotel inspired by the Dewey Decimal System, offering book-filled rooms and an intimate library lounge.
        Open Google Maps Button
        4.6
          Picture for The Library Hotel, New York, NY
        • Hotel Icon

          The Roxbury at Stratton Falls

          Open Google Maps Button

          The Roxbury at Stratton Falls

          Known for its uniquely themed and elaborately decorated rooms, this hotel offers a fun and imaginative lodging experience.
          Open Google Maps Button
            Picture for The Roxbury at Stratton Falls
          • Hotel Icon

            Tarrytown House Estate

            Open Google Maps Button
            4

            Tarrytown House Estate

            A grand historic estate overlooking the Hudson River, combining old-world charm with modern luxury for a unique stay.
            Open Google Maps Button
            4
            Picture for Tarrytown House Estate