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By Huuk Team

Road trip from Charleston to Chesapeake

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Show more (3+)

ITINERARY

8h 27m438 miles18 stops
1
The Black Fedora Comedy Mystery Theatre
164 Church St, Charleston, SC 29401-3125
Live theatre featuring clean comic whodunit shows, volunteer audience participation, a la carte appetizers, homemade desserts, and drinks -- at the downtown City Market. “Uproarious entertainment” - Thrillist.com
2
Escape in 60
45 S Market St, Charleston, SC 29401-2004
Located in beautiful downtown Charleston at the heart of the Market on Market Street. In the middle of all of the action, attractions, restaurants, shops and bars. Escape In 60 is a fun, new entertainment concept to the Charleston. Each Escape Room is a real life adventure game designed for groups. Find hidden clues, solve riddles, puzzles, challenges and more. Take a break from all the Charleston history with an hour of interactive mystery!
3
Edmondston-Alston House
21 E Battery St, Charleston, SC 29401-2740
Constructed nearly 200 years ago, circa 1825, the Edmondston-Alston House presents a unique history of the people, both free and enslaved, who lived and labored on this property. Its collection of furniture, silver and decorative arts, largely original to those who owned the house, constitutes a rich, complex history of Charleston in the 19th century. Commanding a magnificent view of Charleston Harbor, the Edmondston-Alston House has witnessed many historic moments in the port city’s history. One of the oldest houses along the High Battery, it withstood the American Civil War, the Earthquake of 1886, and numerous hurricanes; it has survived to share a piece of Charleston history.
4
The Simpsons in 4D
1199 Celebrity Cir Broadway at the Beach, Myrtle Beach, SC 29577
Established in 2018. The Simpsons in 4D is a fully-themed cinematic attraction located at Broadway at the Beach in Myrtle Beach, South Carolina. Follow @Si4D.Simpsons4D on Instagram and Facebook for updates! The Simpsons in 4D delivers a slice of Springfield with the famous Aztec Theater and Kwik-E-Mart from the groundbreaking television show. The Aztec Theater features a themed lobby experience and a 4D Experience starring Homer and his family. This exciting animated special effects experience with 4D motion seats follows The Simpsons on a fun-filled immersive adventure. Shows run every 15 minutes. The Aztec Theater is a ticketed experience that also includes a souvenir red carpet photo with The Simpsons. Next door, guests can explore and shop at the iconic Kwik-E-Mart The convenience store has been brought to life with select products, including Buzz Soda, Lard Lad Donuts and six show-inspired Squishee flavors, as well as a wide array of custom The Simpsons branded merchandise.
5
Bojangles' Coliseum
2700 E Independence Blvd, Charlotte, NC 28205-6925
Located in Charlotte, NC - Since 1955, Bojangles' Coliseum has hosted concerts, family shows, conferences, sports events, and Charlotte Checkers hockey.
6
Sugar Creek Brewing Company
215 Southside Dr, Charlotte, NC 28217-1727
Sugar Creek Brewing Co. Bringing Belgian-inspired beer to the Carolinas and beyond, Sugar Creek Brewing Company combines the watchful eye of a Trappist Monk with the technical precision of nuclear engineering to craft fresh, full-flavored beers that are immensely satisfying and intensely drinkable. Using unique combinations of aromatic yeast strains, domestic and imported hops and award-winning malt varietys, Sugar Creek infuses traditional recipes with modern tastes and techniques to create beer that nourishes both mind and body. Sugar Creek Tap Room Mon-Wed: 4pm - 9pm Thursday: 4pm - 10pm Friday: 2pm - 10pm Saturday: 11am- 10pm Sunday: 12pm - 8pm Tighten the ropes and raise the sails, the Sugar Creek Brewing Co. Tap room is where your exploration begins! We have constructed a large taproom and private event room and staffed it with kind, courteous and knowledgeable beertenders. On tap you will find all of our year-round beers as well as seasonal and small-batch releases. Beers are available by the glass, 4 oz. Tasting flights, and growler fills via our Pegas CrafTap growler filler. The taproom is open for exploration seven days a week! Sugar Creek Private Event Room Adjacent to our taproom is our 1700 sqft private event room, complete with a private outdoor patio, private bar, and overhead projector. Private events are available seven days a week, for parties as small as 15 people. In addition to offering a full range of our favorite beers, Sugar Creek is happy to provide food services or accommodate outside catering.
7
Wooden Robot Brewery
1440 S Tryon St Suite 110, Charlotte, NC 28203-4262
8
Game On Escapes & More
107 Edinburgh South Dr Suite 203, Cary, NC 27511-8426
We offer family friendly escape games and a game show appealing to a variety of ages. Great for corporate events, team outings, and just a fun night out with friends and family.
9
The Raleigh Market
1025 Blue Ridge Rd, Raleigh, NC 27607-3902
Located on the historic N.C. State Fairgrounds, The Raleigh Market is recognized as one of the Top 10 flea markets in the U.S. Each weekend, indoor and outdoor vendors showcase vintage goods and antiques, collectibles, new items, thrift items, crafts, art, jewelry and so much more. Food trucks, farm stands and fair food ensure customers do not leave hungry! The Raleigh Market is open Saturdays and Sundays, 9 am - 5 pm. Admission and parking are free.
10
Salem Lake
1001 Salem Lake Rd, Winston Salem, NC 27107-1571
11
Deep Creek Park
437 George Washington Hwy S, Chesapeake, VA 23323-6345
12
Pagoda & Oriental Garden
265 W Tazewell St, Norfolk, VA 23510-1209
13
Stumpy Lake Natural Area
4797 Indian River Rd, Virginia Beach, VA 23456-1246
Located along the south central City boundary with Chesapeake, Stumpy Lake Natural Area consists of a 278-acre lake with a raised ADA compliant overlook, 174-acre golf course, with approximately 970+ acres of undeveloped, forested land surrounding the lake and 1.65 miles of soft shared-use trails. As a valuable aesthetic resource, the area offers opportunity for passive recreational uses, such as hiking, fishing, bird watching, nature observation and photography. The 1,422-acre property was acquired in 2001 from the City of Norfolk​. A canoe/kayak launch is located just after the causeway from Indian River Road near the entrance to the Stumpy Lake Golf Course. Designed for non-motorized vessels, the launch is also fully ADA compliant. There is a small picnic shelter nearby. Parking spaces are available for 12 cars and two trailers. Overflow car parking is available at Stumpy Lake Golf Course.
14
O'Connor Brewing Co.
211 W 24th St, Norfolk, VA 23517
The brewery is located at 211 W. 24th Street in the new Railroad district of Norfolk, situated next to the historic Ghent neighborshood and just a mile or two from Downtown. The Tasting Room and Production facility share a 35,000 sq. foot mid-century modern historic building. Free parking is available in their private lot or street parking is free along 24th and 23rd street. O’Connor beer drinkers come from all walks of life, but what brings them together is a love of the small, simple joys in life. The pleasure of being outdoors, relaxing on the beach with friends, having dinner with family after a day of hard work, and of course, enjoying a fresh, flavorful beer. Customers appreciate the O’Connor brand for its approachability and authenticity. They value its independent spirit, that it remains family owned and operated, and its support of the local community. And their loyalty has established it as a mainstay brand with 10 years of sustained success.
15
Veterans United Home Loans Amphitheater
3550 Cellar Door Way, Virginia Beach, VA 23456-6115
16
NEX - Navy Exchange
1560 Mall Dr Bldg #CD-13, Norfolk, VA 23511-3806
17
The Mariners' Museum and Park
100 Museum Drive, Newport News, VA 23606
Curate your Mariners’ Experience! From inspiring stories of mariners who risked it all for freedom to true tales of man conquering the wild seas, our indoor galleries will spark curiosity, wonder, and an appreciation for our shared maritime heritage. Explore over 90,000 square feet of gallery space and discover your connection to our shared maritime heritage. Admission to the Museum is only $1 per person. Add some outdoor adventure to your day in our 550-acre Park which offers visitors a quiet and serene place to walk, hike or run amongst rolling woodlands. Our Park features the award-winning five-mile Noland Trail that surrounds the 167-acre Mariners’ Lake. The Park is free and open to the public.
18
Tagtime Laser Tag
14346 Warwick Blvd Suite 420, Newport News, VA 23602-3814
Tagtime Laser Tag brings you a unique tactical laser tag experience featuring high tech realistic simulated weapons, a 10,000 square foot indoor arena, and all of our games are mission based. Forget what you think you know about Laser Tag, because this isn't it. We promise, you've never played anything like this!
Customize this Trip

OVERVIEW

1
Start:The Black Fedora Comedy Mystery Theatre
Charleston, South Carolina·
4.5
(993) review
Live theatre featuring clean comic whodunit shows, volunteer audience participation, a la carte appetizers, homemade desserts, and drinks -- at the downtown City Market. “Uproarious entertainment” - Thrillist.com
164 Church St, Charleston, SC 29401-3125
2
Escape in 60
Charleston, South Carolina·
5.0
(975) review
Located in beautiful downtown Charleston at the heart of the Market on Market Street. In the middle of all of the action, attractions, restaurants, shops and bars. Escape In 60 is a fun, new entertainment concept to the Charleston. Each Escape Room is a real life adventure game designed for groups. Find hidden clues, solve riddles, puzzles, challenges and more. Take a break from all the Charleston history with an hour of interactive mystery!
45 S Market St, Charleston, SC 29401-2004
3
Edmondston-Alston House
Charleston, South Carolina·
4.5
(992) review
Constructed nearly 200 years ago, circa 1825, the Edmondston-Alston House presents a unique history of the people, both free and enslaved, who lived and labored on this property. Its collection of furniture, silver and decorative arts, largely original to those who owned the house, constitutes a rich, complex history of Charleston in the 19th century. Commanding a magnificent view of Charleston Harbor, the Edmondston-Alston House has witnessed many historic moments in the port city’s history. One of the oldest houses along the High Battery, it withstood the American Civil War, the Earthquake of 1886, and numerous hurricanes; it has survived to share a piece of Charleston history.
21 E Battery St, Charleston, SC 29401-2740
4
The Simpsons in 4D
Myrtle Beach, South Carolina·
4.0
(97) review
Established in 2018. The Simpsons in 4D is a fully-themed cinematic attraction located at Broadway at the Beach in Myrtle Beach, South Carolina. Follow @Si4D.Simpsons4D on Instagram and Facebook for updates! The Simpsons in 4D delivers a slice of Springfield with the famous Aztec Theater and Kwik-E-Mart from the groundbreaking television show. The Aztec Theater features a themed lobby experience and a 4D Experience starring Homer and his family. This exciting animated special effects experience with 4D motion seats follows The Simpsons on a fun-filled immersive adventure. Shows run every 15 minutes. The Aztec Theater is a ticketed experience that also includes a souvenir red carpet photo with The Simpsons. Next door, guests can explore and shop at the iconic Kwik-E-Mart The convenience store has been brought to life with select products, including Buzz Soda, Lard Lad Donuts and six show-inspired Squishee flavors, as well as a wide array of custom The Simpsons branded merchandise.
1199 Celebrity Cir Broadway at the Beach, Myrtle Beach, SC 29577
5
Bojangles' Coliseum
Charlotte, North Carolina·
4.0
(98) review
Located in Charlotte, NC - Since 1955, Bojangles' Coliseum has hosted concerts, family shows, conferences, sports events, and Charlotte Checkers hockey.
2700 E Independence Blvd, Charlotte, NC 28205-6925
6
Sugar Creek Brewing Company
Charlotte, North Carolina·
4.5
(98) review
Sugar Creek Brewing Co. Bringing Belgian-inspired beer to the Carolinas and beyond, Sugar Creek Brewing Company combines the watchful eye of a Trappist Monk with the technical precision of nuclear engineering to craft fresh, full-flavored beers that are immensely satisfying and intensely drinkable. Using unique combinations of aromatic yeast strains, domestic and imported hops and award-winning malt varietys, Sugar Creek infuses traditional recipes with modern tastes and techniques to create beer that nourishes both mind and body. Sugar Creek Tap Room Mon-Wed: 4pm - 9pm Thursday: 4pm - 10pm Friday: 2pm - 10pm Saturday: 11am- 10pm Sunday: 12pm - 8pm Tighten the ropes and raise the sails, the Sugar Creek Brewing Co. Tap room is where your exploration begins! We have constructed a large taproom and private event room and staffed it with kind, courteous and knowledgeable beertenders. On tap you will find all of our year-round beers as well as seasonal and small-batch releases. Beers are available by the glass, 4 oz. Tasting flights, and growler fills via our Pegas CrafTap growler filler. The taproom is open for exploration seven days a week! Sugar Creek Private Event Room Adjacent to our taproom is our 1700 sqft private event room, complete with a private outdoor patio, private bar, and overhead projector. Private events are available seven days a week, for parties as small as 15 people. In addition to offering a full range of our favorite beers, Sugar Creek is happy to provide food services or accommodate outside catering.
215 Southside Dr, Charlotte, NC 28217-1727
7
Wooden Robot Brewery
Charlotte, North Carolina·
4.5
(97) review
1440 S Tryon St Suite 110, Charlotte, NC 28203-4262
8
Game On Escapes & More
Cary, North Carolina·
5.0
(98) review
We offer family friendly escape games and a game show appealing to a variety of ages. Great for corporate events, team outings, and just a fun night out with friends and family.
107 Edinburgh South Dr Suite 203, Cary, NC 27511-8426
9
The Raleigh Market
Raleigh, North Carolina·
4.0
(96) review
Located on the historic N.C. State Fairgrounds, The Raleigh Market is recognized as one of the Top 10 flea markets in the U.S. Each weekend, indoor and outdoor vendors showcase vintage goods and antiques, collectibles, new items, thrift items, crafts, art, jewelry and so much more. Food trucks, farm stands and fair food ensure customers do not leave hungry! The Raleigh Market is open Saturdays and Sundays, 9 am - 5 pm. Admission and parking are free.
1025 Blue Ridge Rd, Raleigh, NC 27607-3902
10
Salem Lake
Winston Salem, North Carolina·
4.5
(97) review
1001 Salem Lake Rd, Winston Salem, NC 27107-1571
11
Deep Creek Park
Chesapeake, Virginia·
4.0
(9) review
437 George Washington Hwy S, Chesapeake, VA 23323-6345
12
Pagoda & Oriental Garden
Norfolk, Virginia·
4.0
(91) review
265 W Tazewell St, Norfolk, VA 23510-1209
13
Stumpy Lake Natural Area
Virginia Beach, Virginia·
4.5
(9) review
Located along the south central City boundary with Chesapeake, Stumpy Lake Natural Area consists of a 278-acre lake with a raised ADA compliant overlook, 174-acre golf course, with approximately 970+ acres of undeveloped, forested land surrounding the lake and 1.65 miles of soft shared-use trails. As a valuable aesthetic resource, the area offers opportunity for passive recreational uses, such as hiking, fishing, bird watching, nature observation and photography. The 1,422-acre property was acquired in 2001 from the City of Norfolk​. A canoe/kayak launch is located just after the causeway from Indian River Road near the entrance to the Stumpy Lake Golf Course. Designed for non-motorized vessels, the launch is also fully ADA compliant. There is a small picnic shelter nearby. Parking spaces are available for 12 cars and two trailers. Overflow car parking is available at Stumpy Lake Golf Course.
4797 Indian River Rd, Virginia Beach, VA 23456-1246
14
O'Connor Brewing Co.
Norfolk, Virginia·
4.5
(97) review
The brewery is located at 211 W. 24th Street in the new Railroad district of Norfolk, situated next to the historic Ghent neighborshood and just a mile or two from Downtown. The Tasting Room and Production facility share a 35,000 sq. foot mid-century modern historic building. Free parking is available in their private lot or street parking is free along 24th and 23rd street. O’Connor beer drinkers come from all walks of life, but what brings them together is a love of the small, simple joys in life. The pleasure of being outdoors, relaxing on the beach with friends, having dinner with family after a day of hard work, and of course, enjoying a fresh, flavorful beer. Customers appreciate the O’Connor brand for its approachability and authenticity. They value its independent spirit, that it remains family owned and operated, and its support of the local community. And their loyalty has established it as a mainstay brand with 10 years of sustained success.
211 W 24th St, Norfolk, VA 23517
15
Veterans United Home Loans Amphitheater
Virginia Beach, Virginia·
3.5
(93) review
3550 Cellar Door Way, Virginia Beach, VA 23456-6115
16
NEX - Navy Exchange
Norfolk, Virginia·
5.0
(9) review
1560 Mall Dr Bldg #CD-13, Norfolk, VA 23511-3806
17
The Mariners' Museum and Park
Newport News, Virginia·
5.0
(959) review
Curate your Mariners’ Experience! From inspiring stories of mariners who risked it all for freedom to true tales of man conquering the wild seas, our indoor galleries will spark curiosity, wonder, and an appreciation for our shared maritime heritage. Explore over 90,000 square feet of gallery space and discover your connection to our shared maritime heritage. Admission to the Museum is only $1 per person. Add some outdoor adventure to your day in our 550-acre Park which offers visitors a quiet and serene place to walk, hike or run amongst rolling woodlands. Our Park features the award-winning five-mile Noland Trail that surrounds the 167-acre Mariners’ Lake. The Park is free and open to the public.
100 Museum Drive, Newport News, VA 23606
18
Tagtime Laser Tag
Newport News, Virginia·
4.5
(9) review
Tagtime Laser Tag brings you a unique tactical laser tag experience featuring high tech realistic simulated weapons, a 10,000 square foot indoor arena, and all of our games are mission based. Forget what you think you know about Laser Tag, because this isn't it. We promise, you've never played anything like this!
14346 Warwick Blvd Suite 420, Newport News, VA 23602-3814

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Charleston and Chesapeake?
The distance is 438 miles
What's the travel time between Charleston and Chesapeake?
The driving time can vary depending on traffic conditions, but it is typically 8h 27m mins in normal traffic
What are some of the best cities to visit between Charleston and Chesapeake?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Chesapeake?
There are plenty! Here are some stops you shouldn’t miss on your way to Chesapeake
What’s the weather like in Chesapeake?
The weather in Chesapeake is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Chesapeake in January
Weather in Chesapeake in February
Weather in Chesapeake in March
Weather in Chesapeake in April
Weather in Chesapeake in May
Weather in Chesapeake in June
Weather in Chesapeake in July
Weather in Chesapeake in August
Weather in Chesapeake in September
Weather in Chesapeake in October
Weather in Chesapeake in November
Weather in Chesapeake in December
Interested in a detailed plan for your time in Chesapeake?
Plan your dream Chesapeake trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Chesapeake
A 2-day itinerary in Chesapeake
A 3-day itinerary in Chesapeake
A 4-day itinerary in Chesapeake
A 5-day itinerary in Chesapeake
A 6-day itinerary in Chesapeake
Where else can I travel to if I'm starting my trip in Charleston?
We have a lot of great trip options for Charleston! See the links below for all the itineraries we created for you