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AI-Magellan
16 Mar 2025Updated last time
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7 Best Places for One Day Trips from Chesapeake, VA

Best One Day Trips from Chesapeake, VA

Chesapeake, Virginia, is an ideal starting point for a variety of enriching and exciting day trips. Whether you're a local looking to explore your own backyard or a visitor eager to discover the region's most compelling destinations, Chesapeake offers convenient access to stunning natural landscapes, historical sites, and vibrant cultural attractions. From the sun-soaked shores of Virginia Beach to the immersive historical experiences at Colonial Williamsburg, and from the botanical wonders of Norfolk Botanical Garden to the serene trails of First Landing State Park, there is something for everyone. Each location promises unique experiences, ensuring your one-day adventure will be memorable and fulfilling. Dive into the details of these must-visit spots, and start planning your perfect day trip!

Recommended Activities

  • Trip Point Pin1

    Virginia Beach

    Virginia Beach offers a beautiful coastline, a vibrant boardwalk, and various outdoor activities such as surfing, fishing, and biking. It's a perfect spot for relaxation and enjoying the ocean.
    Virginia Beach
    Virginia Beach
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    Virginia Beach
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    Virginia Beach
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  • Trip Point Pin2

    Colonial Williamsburg

    Colonial Williamsburg is a living-history museum that provides an immersive experience of America's colonial past. Visitors can explore historic buildings, interact with costumed interpreters, and watch demonstrations of 18th-century crafts and trades.
    Colonial Williamsburg
    Colonial Williamsburg
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    Colonial Williamsburg
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    Colonial Williamsburg
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  • Trip Point Pin3

    Norfolk Botanical Garden

    Norfolk Botanical Garden boasts over 60 themed gardens and miles of walking paths. It's a serene place to explore a vast diversity of plants, enjoy scenic views, and participate in educational programs and seasonal events.
    Norfolk Botanical Garden
    Norfolk Botanical Garden
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    Norfolk Botanical Garden
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    Norfolk Botanical Garden
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    Norfolk Botanical Garden
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  • Trip Point Pin4

    First Landing State Park

    First Landing State Park is rich in history and natural beauty. It offers hiking and biking trails, opportunities for kayaking, and a beautiful beach. It's a great spot for outdoor enthusiasts and history buffs alike.
    First Landing State Park
    First Landing State Park
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    First Landing State Park
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    First Landing State Park
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    First Landing State Park
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    First Landing State Park
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  • Trip Point Pin5

    Jamestown Settlement

    Jamestown Settlement offers a fascinating look into the first permanent English colony in America with interactive exhibits, re-creations of colonial structures, and the chance to board replicas of the three ships that brought settlers to Virginia.
    Jamestown Settlement
    Jamestown Settlement
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    Jamestown Settlement
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    Jamestown Settlement
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    Jamestown Settlement
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    Jamestown Settlement
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    Jamestown Settlement
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    Jamestown Settlement
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  • Trip Point Pin6

    Chesapeake Arboretum

    Chesapeake Arboretum is known as a natural classroom showcasing diverse plant life. It provides picturesque walking trails, gardens, and educational programs, making it a peaceful retreat for nature lovers and garden enthusiasts.
    Chesapeake Arboretum
    Chesapeake Arboretum
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    Chesapeake Arboretum
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    Chesapeake Arboretum
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    Chesapeake Arboretum
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  • Trip Point Pin7

    Great Dismal Swamp National Wildlife Refuge

    Great Dismal Swamp National Wildlife Refuge is a unique and ecologically significant area offering visitors the chance to explore diverse habitats, extensive trails, and Lake Drummond. It's an ideal destination for wildlife observation, bird watching, hiking, and experiencing pristine natural beauty.
    Great Dismal Swamp National Wildlife Refuge
    Great Dismal Swamp National Wildlife Refuge
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    Great Dismal Swamp National Wildlife Refuge
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    Great Dismal Swamp National Wildlife Refuge
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    Great Dismal Swamp National Wildlife Refuge
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Restaurants

  • Restaurant Icon

    Freemason Abbey Restaurant

    3.6
    $$$$

    Freemason Abbey Restaurant

    Housed in a 19th-century church, this unique dining venue offers a charming atmosphere and an extensive menu of American cuisine.
    3.6
    $$$$
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    Grain Rooftop Beer Garden

    4

    Grain Rooftop Beer Garden

    Situated atop Hilton Norfolk The Main, this rooftop restaurant offers stunning views of the city along with a wide selection of craft beers and delicious pub fare.
    4
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    The Birch Bar

    4.7
    $$$$

    The Birch Bar

    Known for its vast selection of rare and unusual craft beers, this cozy bar is a haven for beer enthusiasts looking to try something new.
    4.7
    $$$$
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    Doumar's Cones & Barbecue

    4.4
    $$$$

    Doumar's Cones & Barbecue

    A historic eatery famous for inventing the ice cream cone. Enjoy classic BBQ and old-fashioned ice cream treats in a retro setting.
    4.4
    $$$$
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    The Hunt Room

    4
    $$$$

    The Hunt Room

    Located in the historic Cavalier Hotel, this speakeasy-style bar offers handcrafted cocktails and gourmet small plates in a vintage setting.
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Hotels

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    The Cavalier Hotel - Virginia Beach, Virginia

    The Cavalier Hotel - Virginia Beach, Virginia

    A luxurious historic hotel with stunning architecture, beautifully restored rooms, and exquisite amenities, making it a landmark destination in Virginia Beach.
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    Wedmore Place

    4.6

    Wedmore Place

    A boutique European-style hotel located in the heart of a picturesque vineyard, offering an old-world charm and an immersive wine country experience.
    4.6
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    The Historic Powhatan Resort

    4.3

    The Historic Powhatan Resort

    Set on a former colonial plantation, this resort offers a unique historical setting with spacious accommodations and a variety of recreational facilities.
    4.3
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    The Mariners' Museum Park

    4.8

    The Mariners' Museum Park

    While not a traditional hotel, this site offers a unique camping experience with scenic views, providing an unconventional and adventurous lodging option within a historical park.
    4.8
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    Hilton Norfolk The Main

    4.4

    Hilton Norfolk The Main

    A contemporary hotel known for its upscale amenities, stylish decor, and the rooftop Grain Beer Garden, offering panoramic views of Norfolk's skyline.
    4.4
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Local Events & Happenings

  • Event Icon

    Jo Koy

    Jo Koy

    The event will take place at Chartway Arena at Ted Constant Convocation Center in Norfolk.
    Map IconChartway Arena at Ted Constant Convocation Center in Norfolk (3.77 mi)
    Calendar Icon12 Oct 2025
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    The Black Jacket Symphony Presents The Era of Yacht Rock

    The Black Jacket Symphony Presents The Era of Yacht Rock

    The event will take place at Harrison Opera House in Norfolk.
    Map IconHarrison Opera House in Norfolk (5.93 mi)
    Calendar Icon5 Sep 2025
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  • Event Icon

    HANNAH BERNER: NONE OF MY BUSINESS TOUR

    HANNAH BERNER: NONE OF MY BUSINESS TOUR

    The event will take place at Harrison Opera House in Norfolk.
    Map IconHarrison Opera House in Norfolk (5.93 mi)
    Calendar Icon20 Sep 2025
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  • Event Icon

    Fortune Feimster: Takin' Care of Biscuits Comedy Tour

    Fortune Feimster: Takin' Care of Biscuits Comedy Tour

    The event will take place at Harrison Opera House in Norfolk.
    Map IconHarrison Opera House in Norfolk (5.93 mi)
    Calendar Icon25 Sep 2025
    Website IconVisit Website
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  • Event Icon

    Matt Mathews: Boujee On A Budget Tour

    Matt Mathews: Boujee On A Budget Tour

    The event will take place at Harrison Opera House in Norfolk.
    Map IconHarrison Opera House in Norfolk (5.93 mi)
    Calendar Icon16 Oct 2025
    Website IconVisit Website
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  • Event Icon

    Handel's Messiah with Eric Jacobsen

    Handel's Messiah with Eric Jacobsen

    The event will take place at Harrison Opera House in Norfolk.
    Map IconHarrison Opera House in Norfolk (5.93 mi)
    Calendar Icon20 Dec 2025
    Website IconVisit Website
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    MANIA: The ABBA Tribute

    MANIA: The ABBA Tribute

    The event will take place at Harrison Opera House in Norfolk.
    Map IconHarrison Opera House in Norfolk (5.93 mi)
    Calendar Icon12 Jan 2026
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Travel Gems from Reddit

Music for Your Journey

  • Music Icon

    Tom Petty - Free Fallin'

    Tom Petty - Free Fallin'

    A classic road trip anthem that evokes a sense of open-road freedom and adventure.
    Listen on Spotify
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    Rascal Flatts - Life is a Highway

    Rascal Flatts - Life is a Highway

    An energetic and uplifting track that's perfect for keeping your spirits high during the drive.
    Listen on Spotify
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    Eagles - Take It Easy - 2013 Remaster

    Eagles - Take It Easy - 2013 Remaster

    This mellow tune encourages you to relax and enjoy the journey, making it ideal for scenic drives.
    Listen on Spotify
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    Rihanna - Shut Up And Drive

    Rihanna - Shut Up And Drive

    A fun, upbeat song that adds a playful vibe to your road trip.
    Listen on Spotify
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    Willie Nelson - On The Road Again - Live

    Willie Nelson - On The Road Again - Live

    Another classic road trip song that captures the essence of traveling and exploring new places.
    Listen on Spotify
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    Lynyrd Skynyrd - Sweet Home Alabama

    Lynyrd Skynyrd - Sweet Home Alabama

    This Southern rock hit brings a sense of nostalgia and is perfect for cruising through the countryside.
    Listen on Spotify
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    The Beatles - Drive My Car - Remastered 2009

    The Beatles - Drive My Car - Remastered 2009

    A Beatles classic with a catchy rhythm that's sure to make the drive more enjoyable.
    Listen on Spotify
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    Tom Petty - Runnin' Down A Dream

    Tom Petty - Runnin' Down A Dream

    An energetic song that keeps you motivated and excited about the adventures ahead.
    Listen on Spotify
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  • Music Icon

    Bruce Springsteen - Born to Run

    Bruce Springsteen - Born to Run

    This powerful anthem embodies the spirit of hitting the road and chasing freedom.
    Listen on Spotify
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  • Music Icon

    Twenty One Pilots - Ride

    Twenty One Pilots - Ride

    A smooth and relaxing track that's perfect for winding down as you drive through beautiful scenery.
    Listen on Spotify
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