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16 Mar 2025Updated last time
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Connecticut Road Trip Itinerary

Connecticut Adventure

Embark on an unforgettable Connecticut road trip adventure that will take you through the state's most iconic and fascinating attractions. Begin your journey at the historical Mystic Seaport, one of the largest maritime museums in the world. Here, you can delve into America's seafaring past with historical ships, interactive exhibits, and a recreated 19th-century seafaring village.

Next, explore the enchanting Gillette Castle State Park, home to a unique, medieval-style mansion built by actor William Gillette. Marvel at the intricate architecture and enjoy breathtaking views of the Connecticut River.

Continue your cultural excursion at the Yale University Art Gallery, where you can immerse yourself in a diverse collection of artworks ranging from ancient to modern times. This world-class gallery offers stunning exhibitions and is nestled within the prestigious Yale University.

Don't miss the historic Mark Twain House, the former residence of one of America's greatest authors, Samuel Clemens, known as Mark Twain. Experience guided tours and exhibits that bring Twain's life and literary legacy to life.

Finally, treat yourself to a fantastic shopping experience at the Clinton Crossing Premium Outlets, where you'll find an array of brand-name stores offering significant discounts. This outlet mall is the perfect place to unwind and indulge in some retail therapy.

This carefully curated itinerary promises a well-rounded Connecticut experience, blending history, culture, nature, and shopping into a memorable road trip adventure.


Recommended Activities

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    Mystic Seaport

    Mystic Seaport is one of the largest and most comprehensive maritime museums in the world, offering a unique experience with historical ships, exhibits, and a recreated 19th-century seafaring village.
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    Gillette Castle State Park

    Gillette Castle State Park features a unique, medieval-style mansion built by actor William Gillette, showcasing stunning architecture and offering scenic views of the Connecticut River.
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  • Trip Point Pin3

    Yale University Art Gallery

    Yale University Art Gallery houses a diverse collection of artworks ranging from ancient to modern times, and is known for its world-class exhibitions and beautiful setting within Yale University.
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    Mark Twain House

    The Mark Twain House offers an opportunity to explore the historic home of one of America's greatest authors, Samuel Clemens, known as Mark Twain. Visitors can enjoy guided tours, fascinating exhibits, and learn about Twain's life and work.
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    Clinton Crossing Premium Outlets

    Clinton Crossing Premium Outlets provides a fantastic shopping experience with a wide variety of brand-name stores offering significant discounts. The outdoor setting and convenient location make it a great stop for shopping enthusiasts.
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Restaurants

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    The Place

    4.5
    $$$$

    The Place

    This outdoor eatery offers a unique dining experience where patrons sit on tree stumps around open-air grills, enjoying freshly grilled seafood and other delights.
    4.5
    $$$$
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    Guida's Restaurant

    4.2
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    Guida's Restaurant

    A quirky diner that has been serving locals since the 1940s, known for its nostalgic ambiance and delicious, classic American comfort food.
    4.2
    $$$$
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    The Griswold Inn

    8.7
    $$$$

    The Griswold Inn

    One of the oldest continuously operating inns in the country, offering a historic atmosphere with hearty New England fare.
    8.7
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    Abbott's Lobster in the Rough

    4.2
    $$$$

    Abbott's Lobster in the Rough

    Located by the waterfront in Noank, this gem offers fresh seafood, including their famous lobster rolls, in a laid-back, rustic setting.
    4.2
    $$$$
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    The Schoolhouse at Cannondale

    4.1
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    The Schoolhouse at Cannondale

    Housed in a charming 1872 schoolhouse, this unique restaurant offers farm-to-table cuisine with an emphasis on local and seasonal ingredients.
    4.1
    $$$$
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Hotels

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    Winvian Farm

    4.6

    Winvian Farm

    Set in the Litchfield Hills, this whimsical hotel offers uniquely themed cottages, including options like a treehouse or a helicopter-themed room, providing a one-of-a-kind lodging experience.
    4.6
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    Spicer Mansion

    4.9

    Spicer Mansion

    This luxurious mansion in Mystic offers opulent rooms and exceptional service in a historic setting, making for an unforgettable stay.
    4.9
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    Saybrook Point Resort & Marina

    4.7

    Saybrook Point Resort & Marina

    Located where the Connecticut River meets the Long Island Sound, this hotel features waterfront views, unique guest rooms, and a lighthouse suite for a truly memorable experience.
    4.7
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    Inn at Stonington

    4.9

    Inn at Stonington

    This charming inn offers a cozy, romantic getaway with rooms that overlook the waterfront, perfect for those seeking tranquility and scenic beauty.
    4.9
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    The Whaler's Inn

    4.6

    The Whaler's Inn

    Located in the heart of Mystic, this historic inn combines classic New England charm with modern amenities, offering a unique blend of past and present.
    4.6
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Local Events & Happenings

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    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.
    Map IconToyota Oakdale Theatre in Wallingford (17.37 mi)
    Calendar Icon24 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.
    Map IconToyota Oakdale Theatre in Wallingford (17.37 mi)
    Calendar Icon28 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.
    Map IconDome at Toyota Oakdale Theatre in Wallingford (17.37 mi)
    Calendar Icon30 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.
    Map IconDome at Toyota Oakdale Theatre in Wallingford (17.37 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 (17.37 mi)
    Calendar Icon11 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.
    Map IconToyota Oakdale Theatre in Wallingford (17.37 mi)
    Calendar Icon18 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.
    Map IconToyota Oakdale Theatre in Wallingford (17.37 mi)
    Calendar Icon19 Sep 2025
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Travel Gems from Reddit


Music for Your Journey

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    Rascal Flatts - Life is a Highway

    Rascal Flatts - Life is a Highway

    A classic road trip anthem that will keep your energy high and your spirits lifted as you cruise along.
    Listen on Spotify
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    Willie Nelson - On The Road Again - Live

    Willie Nelson - On The Road Again - Live

    This Willie Nelson hit captures the essence of the joy of traveling and exploring new places.
    Listen on Spotify
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    Eagles - Take It Easy - 2013 Remaster

    Eagles - Take It Easy - 2013 Remaster

    A mellow rock tune that's perfect for winding through scenic roads and enjoying the journey.
    Listen on Spotify
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    Edith Whiskers - Home

    Edith Whiskers - Home

    This comforting song by Edward Sharpe & The Magnetic Zeros is great for moments of reflection and relaxation.
    Listen on Spotify
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    WALK THE MOON - Shut Up and Dance

    WALK THE MOON - Shut Up and Dance

    A lively, fun song that’s sure to energize your drive and get everyone in the car moving.
    Listen on Spotify
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    The Proclaimers - I'm Gonna Be (500 Miles)

    The Proclaimers - I'm Gonna Be (500 Miles)

    A fun, upbeat song that makes any road trip more enjoyable and sing-along worthy.
    Listen on Spotify
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    U2 - Beautiful Day

    U2 - Beautiful Day

    U2’s uplifting track reminds you to savor the beauty of the journey and the world around you.
    Listen on Spotify
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    Talking Heads - Road to Nowhere

    Talking Heads - Road to Nowhere

    This Talking Heads song has a catchy rhythm and a contemplative vibe that suits long drives.
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    Fleetwood Mac - Go Your Own Way - 2004 Remaster

    Fleetwood Mac - Go Your Own Way - 2004 Remaster

    A Fleetwood Mac classic that celebrates freedom and the open road, perfect for any traveler.
    Listen on Spotify
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    Chuck Berry - Route 66

    Chuck Berry - Route 66

    A quintessential road trip song that celebrates the classic American driving route, adding nostalgia to your trip.
    Listen on Spotify
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