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By Huuk Team

Road trip from Leesburg to Bridgeport

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Show more (4+)

ITINERARY

21h 49m1,130 miles32 stops
1
Marion Theatre
50 S Magnolia Ave, Ocala, FL 34471-1153
2
Island H2O Water Park
3230 Inspiration Dr, Kissimmee, FL 34747
Island H2O Water Park is your place for family fun! Tube slides, raft riding & splash zones, plus luxury cabana rentals at a sprawling water park.
3
The Legends Walk Course
8505 W Irlo Bronson Memorial Hwy Orange Lake Resort, Kissimmee, FL 34747-8217
4
Teatro Martini
6400 Carrier Dr, Orlando, FL 32819-8260
When the sun goes down at the circus, the acts get hotter, the laughs get bigger, and everything gets a whole lot crazier. Award winning acts from around the world will amaze and astound while the best of the best perform on the stage and all around you. Laugh till you can’t breath, watch till you can’t believe, and celebrate what happens when you finally get to see Teatro Martini. Located in Orlando, Florida, in the heart of I-Drive, this highly interactive show features circus performers from around the world including comedy magician, clowns, acrobats and performing puppies!
5
1001 Transportation
6401 Time Square Ave Cu-20 #1022, Orlando, FL 32819-9118
Airport Transportation Affordable flat rate Orlando & Miami ground transportation with over 20 years of combined experience. Our chauffeurs have earned an excellent reputation for exceptional standard of safety, reliability and professionalism Transportation in Orlando & Miami Florida.
6
Ocala Palms Golf & Country Club
5174 NW 26th St, Ocala, FL 34482-3250
7
Corpus Christi Catholic Church
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
8
Young's Paso Fino Ranch
7950 NW 80th Ave, Ocala, FL 34482-1112
9
Depot Park
200 SE Depot Ave, Gainesville, FL 32601-7004
Depot Park is a signature city park in downtown Gainesville providing a space for unique public outdoor enjoyment. Depot features a children's adventure play area with a custom splash pad of waterfalls, water soakers, and ground jets. A water's edge promenade hosts special events like food truck rallies, art festivals, and musical performances. The park is fully staffed and free of charge.
10
Underbelly
113 E Bay St, Jacksonville, FL 32202-3414
Located in the heart of Downtown, in Jacksonville's "Elbow District", Underbelly isn't just a building and a stage where people come to enjoy music. It's much bigger than that. It's not the paint on the walls. It's not the brick, wood, and nails that hold it all together. It's not the lights or the electricity that define it. Underbelly is a garden. A place for people, regardless of who you are or what you do, to just leave it all at the door for a small while. It's a place for humans. People wanting to be just that. Surrounded by others that feel the same to come together for however long it may be, to be here and now - no more, no less. It's a place where the best musicians unite to create moments that exist nowhere else. Isn't that what it is all about? Finding those moments of magic that will stay with you forever? Well, that's what we sell. We sell magic in all sizes. So come with many, come with none, it doesn't matter. Because when you're here, you're home.
11
Downtown Cigar Lounge
11 N Ocean St, Jacksonville, FL 32202-3311
Location in the heart of downtown Jacksonville in a 101 year-old historic building. We are home to a diverse selection of premium hand-rolled cigars from various regions and a variety of wines, beers and specialty drinks . DCL is not only about cigars we are also a gallery displaying the artwork of local artists.
12
Regal River City Marketplace Stadium 14
12884 City Center Blvd River City Marketplace, Jacksonville, FL 32218-7216
13
Cathedral of St. John the Baptist
222 E Harris St, Savannah, GA 31401-4616
The oldest Roman Catholic church in Georgia.
14
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.
15
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
16
Rockwood Park
3401 Courthouse Rd, Richmond, VA 23236-1438
17
St. Paul's Episcopal Church
815 E Grace St, Richmond, VA 23219-3409
18
Howard Peters Rawlings Conservatory and Botanic Gardens of Baltimore
3100 Swann Dr Druid Hill Park, Baltimore, MD 21217
19
Baltimore Spirits Company
1700 W 41st St Ste 430, Union Collective, Baltimore, MD 21211-1674
Be the master blender for the day! Blend your own bottle of Epoch Maryland Rye, Baltimore's first Maryland Rye to be produced in the city since the 1970s. In this unforgettable experience, your tour and blending experience will take between 1.5 and 2 hours. The highlight of the afternoon will be to taste and evaluate four of our barrel-finished Maryland Rye whiskeys, and then to create your own custom blended bottle of the spirits. Epoch Rye won Double-Gold Medals at both the 2018 and 2020 San Francisco World Spirits Competition. We take care of you from the time you walk in the door to ensure your perfect date, afternoon with friends, or a great gift for a whiskey fan. In addition to creating your own custom blend of our award-winning Pot-Distilled Maryland Rye, attendees also receive: • One delicious welcome cocktail • A compelling history lesson of Maryland Rye (15 minutes) • An up-close and personal distillery tour of our production facility and 650+ barrel rickhouse.
20
Cylburn Arboretum
4915 Greenspring Ave, Baltimore, MD 21209-4698
21
Baltimore Clayworks
5706 Smith Ave, Baltimore, MD 21209-3663
22
John Heinz National Wildlife Refuge at Tinicum
86th Street Lindberg Boulevard, Philadelphia, PA 19143
Visit John Heinz National Wildlife Refuge at Tinicum! Come enjoy 10 miles of walking trails through wooded forests, an impoundment pond, and 300 acres of the largest remaining freshwater tidal marsh in PA. Visitors can also experience the marsh on the water through 4.5 mile of Darby Creek by canoe or kayak. Stop by the front desk to borrow binoculars or fishing rods. Refuge trails are open every day from sunrise to sunset, free of charge. The Visitor Center is open daily from 8:30 AM to 4:00 PM. The visitor center building is closed for all Federal holidays however the trails remain open. Darby Creek is tidal and navigable only within 2 hours before and after high tide. Boat Launch is located at the trailhead of Dike Trail. Visitors must provide their own canoe/kayak and life vests. John Heinz NWR offers year-round free recreational and educational programs.
23
Arthur Ross Gallery
In the Fisher Fine Arts Library 220 South 34th Street, Philadelphia, PA 19104
24
Old City Hall
Independence Mall, Philadelphia, PA 19106
25
Dave & Buster's - Arcade
325 N Columbus Blvd, Philadelphia, PA 19106-1416
At Dave & Buster's you can play hundreds of the hottest new arcade games in our Million Dollar Midway and win tickets for epic prizes. Try our mouth-watering, chef-crafted creations in our American restaurant. From wings to steaks, we've got whatever suits your appetite. Our premium sports bar features innovative cocktails, impressive wine selection, and 20+ beers to assure we're stocked to satisfy! Watch your team on one of our massive HDTVs with epic stadium sound that surrounds you from every direction in the sports bar that crushes the competition. Invite all your friends or coworkers for an unforgettable party or event! We work with every size and budget to make planning easy so you can focus on the FUN!
26
BrainXcape
160 Broadway 3rd Fl, New York City, NY 10038
27
Daniel Roy's Parlour Of Deceptions
47 5th Avenue, New York City, NY 10003
Join magician Daniel Roy at the exclusive Salmagundi Club of New York City for an evening of sleight-of-hand, misdirection, and magic. Limited to just 40 guests, this is an intimate experience of wonder. While this is not a kids show and the magic is geared towards adults, the performance is entirely “clean” and appropriate for audience members age 13 years and older.
28
The Blue Bar, Algonquin Hotel
59 W 44th St, New York City, NY 10036-6613
Comfortable and classic, the lounge of the Algonquin Hotel is a New York landmark.
29
Precision NY Chauffeur & Airport Transportation Services
1177 Avenue Of Americas 5th Floor, New York City, NY 10036
Here at Precision NY Chauffeur & Airport Transportation Service, we offer limousine service and point to point transportation NYC. You can always depend on us for reliable transportation New York, New Jersey, Westchester, Connecticut, Washington DC, Pennsylvania, and Boston. Along with equitable rates and attentive service, we offer transfer services anywhere within the country. For your convenience, you may reserve any vehicle from our fleet vehicles up to 24 hours in advance, including the Lincoln MKT, Lincoln Town Car and Cadillac XTS. For larger parties or a more comfortable ride, we have Cadillac™ Escalades, Lincoln™ Navigators, and Chevy™ Suburbans. We also carry New 2023 and 2024 Mercedes S560s.
30
New Haven Railroad Station
50 Union Ave, New Haven, CT 06519-1754
31
Yale University Art Gallery
1111 Chapel Street, New Haven, CT 06510-2301
Yale University Art Gallery is the oldest college art museum in America. The Gallery’s encyclopedic holdings of more than 250,000 objects range from ancient times to the present day and represent civilizations from around the globe. Spanning a block and a half of the city of New Haven, Connecticut, the Gallery comprises three architecturally distinct buildings, including a masterpiece of modern architecture from 1953 designed by Louis Kahn through which visitors enter. The museum is free and open to the public.
32
David S. Ingalls Rink
73 Sachem St, New Haven, CT 06511-3518
Customize this Trip

OVERVIEW

Leesburg to Bridgeport
1
Start:Marion Theatre
Ocala, Florida·
4.5
(90) review
50 S Magnolia Ave, Ocala, FL 34471-1153
2
Island H2O Water Park
Kissimmee, Florida·
3.5
(96) review
Island H2O Water Park is your place for family fun! Tube slides, raft riding & splash zones, plus luxury cabana rentals at a sprawling water park.
3230 Inspiration Dr, Kissimmee, FL 34747
3
The Legends Walk Course
Kissimmee, Florida·
4.0
(96) review
8505 W Irlo Bronson Memorial Hwy Orange Lake Resort, Kissimmee, FL 34747-8217
4
Teatro Martini
Orlando, Florida·
4.5
(960) review
When the sun goes down at the circus, the acts get hotter, the laughs get bigger, and everything gets a whole lot crazier. Award winning acts from around the world will amaze and astound while the best of the best perform on the stage and all around you. Laugh till you can’t breath, watch till you can’t believe, and celebrate what happens when you finally get to see Teatro Martini. Located in Orlando, Florida, in the heart of I-Drive, this highly interactive show features circus performers from around the world including comedy magician, clowns, acrobats and performing puppies!
6400 Carrier Dr, Orlando, FL 32819-8260
5
1001 Transportation
Orlando, Florida·
5.0
(98) review
Airport Transportation Affordable flat rate Orlando & Miami ground transportation with over 20 years of combined experience. Our chauffeurs have earned an excellent reputation for exceptional standard of safety, reliability and professionalism Transportation in Orlando & Miami Florida.
6401 Time Square Ave Cu-20 #1022, Orlando, FL 32819-9118
6
Ocala Palms Golf & Country Club
Ocala, Florida·
4.5
(9) review
5174 NW 26th St, Ocala, FL 34482-3250
7
Corpus Christi Catholic Church
Celebration, Orlando, Florida·
5.0
(99) review
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
8
Young's Paso Fino Ranch
Ocala, Florida·
4.0
(9) review
7950 NW 80th Ave, Ocala, FL 34482-1112
9
Depot Park
Gainesville, Florida·
5.0
(94) review
Depot Park is a signature city park in downtown Gainesville providing a space for unique public outdoor enjoyment. Depot features a children's adventure play area with a custom splash pad of waterfalls, water soakers, and ground jets. A water's edge promenade hosts special events like food truck rallies, art festivals, and musical performances. The park is fully staffed and free of charge.
200 SE Depot Ave, Gainesville, FL 32601-7004
10
Underbelly
Jacksonville, Florida·
3.5
(9) review
Located in the heart of Downtown, in Jacksonville's "Elbow District", Underbelly isn't just a building and a stage where people come to enjoy music. It's much bigger than that. It's not the paint on the walls. It's not the brick, wood, and nails that hold it all together. It's not the lights or the electricity that define it. Underbelly is a garden. A place for people, regardless of who you are or what you do, to just leave it all at the door for a small while. It's a place for humans. People wanting to be just that. Surrounded by others that feel the same to come together for however long it may be, to be here and now - no more, no less. It's a place where the best musicians unite to create moments that exist nowhere else. Isn't that what it is all about? Finding those moments of magic that will stay with you forever? Well, that's what we sell. We sell magic in all sizes. So come with many, come with none, it doesn't matter. Because when you're here, you're home.
113 E Bay St, Jacksonville, FL 32202-3414
11
Downtown Cigar Lounge
Jacksonville, Florida·
4.5
(9) review
Location in the heart of downtown Jacksonville in a 101 year-old historic building. We are home to a diverse selection of premium hand-rolled cigars from various regions and a variety of wines, beers and specialty drinks . DCL is not only about cigars we are also a gallery displaying the artwork of local artists.
11 N Ocean St, Jacksonville, FL 32202-3311
12
Regal River City Marketplace Stadium 14
Jacksonville, Florida·
4.5
(9) review
12884 City Center Blvd River City Marketplace, Jacksonville, FL 32218-7216
13
Cathedral of St. John the Baptist
Savannah, Georgia·
5.0
(9819) review
The oldest Roman Catholic church in Georgia.
222 E Harris St, Savannah, GA 31401-4616
14
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
15
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
16
Rockwood Park
Richmond, Virginia·
5.0
(9) review
3401 Courthouse Rd, Richmond, VA 23236-1438
17
St. Paul's Episcopal Church
Richmond, Virginia·
4.5
(94) review
815 E Grace St, Richmond, VA 23219-3409
18
Howard Peters Rawlings Conservatory and Botanic Gardens of Baltimore
Baltimore, Maryland·
4.5
(99) review
3100 Swann Dr Druid Hill Park, Baltimore, MD 21217
19
Baltimore Spirits Company
Baltimore, Maryland·
5.0
(9) review
Be the master blender for the day! Blend your own bottle of Epoch Maryland Rye, Baltimore's first Maryland Rye to be produced in the city since the 1970s. In this unforgettable experience, your tour and blending experience will take between 1.5 and 2 hours. The highlight of the afternoon will be to taste and evaluate four of our barrel-finished Maryland Rye whiskeys, and then to create your own custom blended bottle of the spirits. Epoch Rye won Double-Gold Medals at both the 2018 and 2020 San Francisco World Spirits Competition. We take care of you from the time you walk in the door to ensure your perfect date, afternoon with friends, or a great gift for a whiskey fan. In addition to creating your own custom blend of our award-winning Pot-Distilled Maryland Rye, attendees also receive: • One delicious welcome cocktail • A compelling history lesson of Maryland Rye (15 minutes) • An up-close and personal distillery tour of our production facility and 650+ barrel rickhouse.
1700 W 41st St Ste 430, Union Collective, Baltimore, MD 21211-1674
20
Cylburn Arboretum
Baltimore, Maryland·
4.5
(91) review
4915 Greenspring Ave, Baltimore, MD 21209-4698
21
Baltimore Clayworks
Baltimore, Maryland·
4.5
(9) review
5706 Smith Ave, Baltimore, MD 21209-3663
22
John Heinz National Wildlife Refuge at Tinicum
Philadelphia, Pennsylvania·
4.5
(93) review
Visit John Heinz National Wildlife Refuge at Tinicum! Come enjoy 10 miles of walking trails through wooded forests, an impoundment pond, and 300 acres of the largest remaining freshwater tidal marsh in PA. Visitors can also experience the marsh on the water through 4.5 mile of Darby Creek by canoe or kayak. Stop by the front desk to borrow binoculars or fishing rods. Refuge trails are open every day from sunrise to sunset, free of charge. The Visitor Center is open daily from 8:30 AM to 4:00 PM. The visitor center building is closed for all Federal holidays however the trails remain open. Darby Creek is tidal and navigable only within 2 hours before and after high tide. Boat Launch is located at the trailhead of Dike Trail. Visitors must provide their own canoe/kayak and life vests. John Heinz NWR offers year-round free recreational and educational programs.
86th Street Lindberg Boulevard, Philadelphia, PA 19143
23
Arthur Ross Gallery
Philadelphia, Pennsylvania·
4.0
(9) review
In the Fisher Fine Arts Library 220 South 34th Street, Philadelphia, PA 19104
24
Old City Hall
Philadelphia, Pennsylvania·
4.5
(99) review
Independence Mall, Philadelphia, PA 19106
25
Dave & Buster's - Arcade
Philadelphia, Pennsylvania·
3.0
(98) review
At Dave & Buster's you can play hundreds of the hottest new arcade games in our Million Dollar Midway and win tickets for epic prizes. Try our mouth-watering, chef-crafted creations in our American restaurant. From wings to steaks, we've got whatever suits your appetite. Our premium sports bar features innovative cocktails, impressive wine selection, and 20+ beers to assure we're stocked to satisfy! Watch your team on one of our massive HDTVs with epic stadium sound that surrounds you from every direction in the sports bar that crushes the competition. Invite all your friends or coworkers for an unforgettable party or event! We work with every size and budget to make planning easy so you can focus on the FUN!
325 N Columbus Blvd, Philadelphia, PA 19106-1416
26
BrainXcape
New York City, New York·
5.0
(99) review
160 Broadway 3rd Fl, New York City, NY 10038
27
Daniel Roy's Parlour Of Deceptions
New York City, New York·
5.0
(99) review
Join magician Daniel Roy at the exclusive Salmagundi Club of New York City for an evening of sleight-of-hand, misdirection, and magic. Limited to just 40 guests, this is an intimate experience of wonder. While this is not a kids show and the magic is geared towards adults, the performance is entirely “clean” and appropriate for audience members age 13 years and older.
47 5th Avenue, New York City, NY 10003
28
The Blue Bar, Algonquin Hotel
New York City, New York·
4.0
(99) review
Comfortable and classic, the lounge of the Algonquin Hotel is a New York landmark.
59 W 44th St, New York City, NY 10036-6613
29
Precision NY Chauffeur & Airport Transportation Services
New York City, New York·
5.0
(99) review
Here at Precision NY Chauffeur & Airport Transportation Service, we offer limousine service and point to point transportation NYC. You can always depend on us for reliable transportation New York, New Jersey, Westchester, Connecticut, Washington DC, Pennsylvania, and Boston. Along with equitable rates and attentive service, we offer transfer services anywhere within the country. For your convenience, you may reserve any vehicle from our fleet vehicles up to 24 hours in advance, including the Lincoln MKT, Lincoln Town Car and Cadillac XTS. For larger parties or a more comfortable ride, we have Cadillac™ Escalades, Lincoln™ Navigators, and Chevy™ Suburbans. We also carry New 2023 and 2024 Mercedes S560s.
1177 Avenue Of Americas 5th Floor, New York City, NY 10036
30
New Haven Railroad Station
New Haven, Connecticut·
4.0
(97) review
50 Union Ave, New Haven, CT 06519-1754
31
Yale University Art Gallery
New Haven, Connecticut·
5.0
(984) review
Yale University Art Gallery is the oldest college art museum in America. The Gallery’s encyclopedic holdings of more than 250,000 objects range from ancient times to the present day and represent civilizations from around the globe. Spanning a block and a half of the city of New Haven, Connecticut, the Gallery comprises three architecturally distinct buildings, including a masterpiece of modern architecture from 1953 designed by Louis Kahn through which visitors enter. The museum is free and open to the public.
1111 Chapel Street, New Haven, CT 06510-2301
32
David S. Ingalls Rink
New Haven, Connecticut·
4.5
(9) review
73 Sachem St, New Haven, CT 06511-3518

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FAQ
Frequently Asked Questions
What's the driving distance between Leesburg and Bridgeport?
The distance is 1,130 miles
What's the travel time between Leesburg and Bridgeport?
The driving time can vary depending on traffic conditions, but it is typically 21h 49m mins in normal traffic
What are some of the best cities to visit between Leesburg and Bridgeport?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Bridgeport?
There are plenty! Here are some stops you shouldn’t miss on your way to Bridgeport
What’s the weather like in Bridgeport?
The weather in Bridgeport is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Bridgeport in January
Weather in Bridgeport in February
Weather in Bridgeport in March
Weather in Bridgeport in April
Weather in Bridgeport in May
Weather in Bridgeport in June
Weather in Bridgeport in July
Weather in Bridgeport in August
Weather in Bridgeport in September
Weather in Bridgeport in October
Weather in Bridgeport in November
Weather in Bridgeport in December
Interested in a detailed plan for your time in Bridgeport?
Plan your dream Bridgeport trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Bridgeport
A 2-day itinerary in Bridgeport
A 3-day itinerary in Bridgeport
A 4-day itinerary in Bridgeport
A 5-day itinerary in Bridgeport
A 6-day itinerary in Bridgeport
Where else can I travel to if I'm starting my trip in Leesburg?
We have a lot of great trip options for Leesburg! See the links below for all the itineraries we created for you