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AI-Magellan
16 Mar 2025Updated last time
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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.

Recommended Activities

  • 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.
    Mystic Seaport
    Mystic Seaport
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    New Haven

    New Haven is home to Yale University, offering rich cultural and historical landmarks, renowned museums, vibrant arts scenes, and diverse dining options.
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    New Haven
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    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.
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    Hammonasset Beach State Park
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    Hammonasset Beach State Park
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    Hammonasset Beach State Park
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    Hammonasset Beach State Park
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    Hammonasset Beach State Park
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    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.
    Bear Mountain State Park
    Bear Mountain State Park
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    Bear Mountain State Park
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  • 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.
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    Kent Falls State Park
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    Kent Falls State Park
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    Kent Falls State Park
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    Kent Falls State Park
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    Kent Falls State Park
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    Kent Falls State Park
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    Kent Falls State Park
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    Kent Falls State Park
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    Kent Falls State Park
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    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.
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    The Berkshires
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    The Berkshires
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    The Berkshires
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  • 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.
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    Old Saybrook
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    Newport

    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.
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    Newport
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    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.
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    Litchfield Hills
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    Litchfield Hills
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  • 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.
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    Mohonk Mountain House
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    Mohonk Mountain House
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Restaurants

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    The Singing Chef

    The Singing Chef

    A unique dining experience where the chef performs live operatic songs while preparing gourmet Italian dishes.
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    The Place Restaurant

    4.5
    $$$$

    The Place Restaurant

    An outdoor roadside eatery where you can enjoy fresh seafood and barbecue cooked over an open fire, and dine in rustic surroundings.
    4.5
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    Mystic Pizza

    3.9
    $$$$

    Mystic Pizza

    Made famous by the 1988 film of the same name, this cozy spot serves delicious pizzas with a nostalgic Hollywood vibe.
    3.9
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    Harvest Moon Orchard & Cidery

    4.3

    Harvest Moon Orchard & Cidery

    A charming farm-to-table restaurant offering seasonal dishes and craft ciders in a picturesque orchard setting.
    4.3
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    Glenmere Mansion

    4.8

    Glenmere Mansion

    A luxurious dining experience in a historic mansion, featuring gourmet cuisine and stunning Hudson Valley views.
    4.8
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Hotels

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    Winvian Farm

    Winvian Farm

    A collection of whimsical, themed cottages set on a 113-acre farm, each offering a uniquely creative lodging experience.
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    The Roundhouse at Beacon Falls

    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.
    4.2
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    The Library Hotel, New York, NY

    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.
    4.6
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    The Roxbury at Stratton Falls

    The Roxbury at Stratton Falls

    Known for its uniquely themed and elaborately decorated rooms, this hotel offers a fun and imaginative lodging experience.
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    Tarrytown House Estate

    4

    Tarrytown House Estate

    A grand historic estate overlooking the Hudson River, combining old-world charm with modern luxury for a unique stay.
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Local Events & Happenings

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    The Plot In You: AMERICAN TOUR 2025

    The Plot In You: AMERICAN TOUR 2025

    The DOME at Toyota Oakdale Theatre offers General Admission/Standing Room only tickets. Guests who are in need of an ADA or Accessible Seating accommodation will purchase a GA ticket and will be assisted on the day of the show once inside the venue.
    Map IconDome at Toyota Oakdale Theatre in Wallingford (8.27 mi)
    Calendar Icon6 Sep 2025
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    Danny Go! Live!

    Danny Go! Live!

    Danny Go! is a live-action educational childrens show filled with music, movement and silliness. Created in 2019 by 3 childhood friends in Charlotte, North Carolina, the show inspires learning and off-the-couch exercise for kids ages 3 to 7. Any atte...
    Map IconToyota Oakdale Theatre in Wallingford (8.27 mi)
    Calendar Icon11 Sep 2025
    Website IconVisit Website
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    Russell Dickerson - RUSSELLMANIA Tour

    Russell Dickerson - RUSSELLMANIA Tour

    The event will take place at Toyota Oakdale Theatre in Wallingford.
    Map IconToyota Oakdale Theatre in Wallingford (8.27 mi)
    Calendar Icon18 Sep 2025
    Website IconVisit Website
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    The Best of The Eagles

    The Best of The Eagles

    The event will take place at Toyota Oakdale Theatre in Wallingford.
    Map IconToyota Oakdale Theatre in Wallingford (8.27 mi)
    Calendar Icon19 Sep 2025
    Website IconVisit Website
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    The Witcher in Concert

    The Witcher in Concert

    The event will take place at Toyota Oakdale Theatre in Wallingford.
    Map IconToyota Oakdale Theatre in Wallingford (8.27 mi)
    Calendar Icon21 Sep 2025
    Website IconVisit Website
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    CoComelon Photo Experience **NOT A CONCERT TICKET**

    CoComelon Photo Experience **NOT A CONCERT TICKET**

    Meet the Characters of CoCoMelon: Sing-A-Long LIVE! In this exclusive post show experience, you and your family will have the opportunity to make a lasting memory of your visit by taking a photo alongside Ms Appleberry and JJ! Heres how it works: Pho...
    Map IconToyota Oakdale Theatre in Wallingford (8.27 mi)
    Calendar Icon26 Sep 2025
    Website IconVisit Website
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    Premium Box Seat CoComelon Sing-A-Long LIVE

    Premium Box Seat CoComelon Sing-A-Long LIVE

    The event will take place at Toyota Oakdale Theatre in Wallingford.
    Map IconToyota Oakdale Theatre in Wallingford (8.27 mi)
    Calendar Icon26 Sep 2025
    Website IconVisit Website
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Travel Gems from Reddit

Music for Your Journey

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    Eagles - Take It Easy - 2013 Remaster

    Eagles - Take It Easy - 2013 Remaster

    A classic road trip anthem that sets a relaxed and easygoing mood.
    Listen on Spotify
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    Willie Nelson - On The Road Again - Live

    Willie Nelson - On The Road Again - Live

    A timeless tune that captures the excitement of being back on the road.
    Listen on Spotify
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    Rascal Flatts - Life is a Highway

    Rascal Flatts - Life is a Highway

    This high-energy track is perfect for keeping your spirits high as you drive.
    Listen on Spotify
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    Chuck Berry - Route 66

    Chuck Berry - Route 66

    An American classic that celebrates the freedom and adventure of traveling.
    Listen on Spotify
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    Rihanna - Shut Up And Drive

    Rihanna - Shut Up And Drive

    A lively, upbeat song to rev up your road trip.
    Listen on Spotify
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    Rusted Root - Send Me on My Way

    Rusted Root - Send Me on My Way

    This feel-good song will inspire a sense of adventure and curiosity on your trip.
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    Fleetwood Mac - Go Your Own Way - 2004 Remaster

    Fleetwood Mac - Go Your Own Way - 2004 Remaster

    An anthem of independence and making your own path, perfect for a getaway.
    Listen on Spotify
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    The Beatles - Drive My Car - Remastered 2009

    The Beatles - Drive My Car - Remastered 2009

    A catchy and upbeat tune that adds fun to any car ride.
    Listen on Spotify
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    Whitesnake - Here I Go Again - 2018 Remaster

    Whitesnake - Here I Go Again - 2018 Remaster

    A powerful rock ballad that speaks to the journey and the unknown ahead.
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    Tom Petty - Free Fallin'

    Tom Petty - Free Fallin'

    This laid-back song is ideal for moments of peaceful reflection on the road.
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