Virginia

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

1
Virginia Beach
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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.
2
Colonial Williamsburg
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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.
3
Norfolk Botanical Garden
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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.
4
First Landing State Park
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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.
5
Jamestown Settlement
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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.
6
Chesapeake Arboretum
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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.
7
Great Dismal Swamp National Wildlife Refuge
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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.

Restaurants

Freemason Abbey Restaurant
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3.6
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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
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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
The Birch Bar
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4.7
$$$$
The Birch Bar
Known for its vast selection of rare and unusual craft beers, this cozy bar is a haven for beer enthusiasts looking to try something new.
4.7
$$$$
Doumar's Cones & Barbecue
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4.4
$$$$
Doumar's Cones & Barbecue
A historic eatery famous for inventing the ice cream cone. Enjoy classic BBQ and old-fashioned ice cream treats in a retro setting.
4.4
$$$$
The Hunt Room
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4
$$$$
The Hunt Room
Located in the historic Cavalier Hotel, this speakeasy-style bar offers handcrafted cocktails and gourmet small plates in a vintage setting.
4
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Hotels

The Cavalier Hotel - Virginia Beach, Virginia
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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.
Wedmore Place
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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
The Historic Powhatan Resort
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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
The Mariners' Museum Park
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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
Hilton Norfolk The Main
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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

Local Events & Happenings

Jo Koy
Jo Koy
The event will take place at Chartway Arena at Ted Constant Convocation Center in Norfolk.
Chartway Arena at Ted Constant Convocation Center in Norfolk (3.77 mi)
12 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.
Harrison Opera House in Norfolk (5.93 mi)
5 Sep 2025
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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.
Harrison Opera House in Norfolk (5.93 mi)
20 Sep 2025
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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.
Harrison Opera House in Norfolk (5.93 mi)
25 Sep 2025
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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.
Harrison Opera House in Norfolk (5.93 mi)
16 Oct 2025
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Handel's Messiah with Eric Jacobsen
Handel's Messiah with Eric Jacobsen
The event will take place at Harrison Opera House in Norfolk.
Harrison Opera House in Norfolk (5.93 mi)
20 Dec 2025
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MANIA: The ABBA Tribute
MANIA: The ABBA Tribute
The event will take place at Harrison Opera House in Norfolk.
Harrison Opera House in Norfolk (5.93 mi)
12 Jan 2026
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