Connecticut

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

1
Mystic Seaport
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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.
2
New Haven
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New Haven is home to Yale University, offering rich cultural and historical landmarks, renowned museums, vibrant arts scenes, and diverse dining options.
3
Hammonasset Beach State Park
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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.
4
Bear Mountain State Park
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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.
5
Kent Falls State Park
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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.
6
The Berkshires
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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.
7
Old Saybrook
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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.
8
Newport
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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.
9
Litchfield Hills
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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.
10
Mohonk Mountain House
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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.

Restaurants

The Singing Chef
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The Singing Chef
A unique dining experience where the chef performs live operatic songs while preparing gourmet Italian dishes.
The Place Restaurant
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4.5
$$$$
The Place Restaurant
An outdoor roadside eatery where you can enjoy fresh seafood and barbecue cooked over an open fire, and dine in rustic surroundings.
4.5
$$$$
Mystic Pizza
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3.9
$$$$
Mystic Pizza
Made famous by the 1988 film of the same name, this cozy spot serves delicious pizzas with a nostalgic Hollywood vibe.
3.9
$$$$
Harvest Moon Orchard & Cidery
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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
Glenmere Mansion
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4.8
Glenmere Mansion
A luxurious dining experience in a historic mansion, featuring gourmet cuisine and stunning Hudson Valley views.
4.8

Stay Recommendations

Winvian Farm
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Winvian Farm
A collection of whimsical, themed cottages set on a 113-acre farm, each offering a uniquely creative lodging experience.
The Roundhouse at Beacon Falls
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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
The Library Hotel, New York, NY
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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
The Roxbury at Stratton Falls
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The Roxbury at Stratton Falls
Known for its uniquely themed and elaborately decorated rooms, this hotel offers a fun and imaginative lodging experience.
Tarrytown House Estate
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4
Tarrytown House Estate
A grand historic estate overlooking the Hudson River, combining old-world charm with modern luxury for a unique stay.
4

Local Events & Happenings

Völkerball- Germany's Best Rammstein Tribute Band
Völkerball- Germany's Best Rammstein Tribute Band
The event will take place at Toyota Oakdale Theatre in Wallingford.
Toyota Oakdale Theatre in Wallingford (8.27 mi)
24 Aug 2025
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Chevelle with special guests Asking Alexandria and Dead Poet Society
Chevelle with special guests Asking Alexandria and Dead Poet Society
The event will take place at Toyota Oakdale Theatre in Wallingford.
Toyota Oakdale Theatre in Wallingford (8.27 mi)
28 Aug 2025
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R&B ONLY LIVE - Wallingford, CT (10 Year Anniversary)
R&B ONLY LIVE - Wallingford, CT (10 Year Anniversary)
The event will take place at Dome at Toyota Oakdale Theatre in Wallingford.
Dome at Toyota Oakdale Theatre in Wallingford (8.27 mi)
30 Aug 2025
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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.
Dome at Toyota Oakdale Theatre in Wallingford (8.27 mi)
6 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...
Toyota Oakdale Theatre in Wallingford (8.27 mi)
11 Sep 2025
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Russell Dickerson - RUSSELLMANIA Tour
Russell Dickerson - RUSSELLMANIA Tour
The event will take place at Toyota Oakdale Theatre in Wallingford.
Toyota Oakdale Theatre in Wallingford (8.27 mi)
18 Sep 2025
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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.
Toyota Oakdale Theatre in Wallingford (8.27 mi)
19 Sep 2025
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