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By Huuk Team

Road trip from Bridgeport to Leesburg

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iconSights & Landmarks
iconWater & Amusement Parks
iconOutdoor Activities
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iconFun & Games
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iconNightlife
Show more (3+)

ITINERARY

21h 54m1,138 miles21 stops
1
New Haven Railroad Station
50 Union Ave, New Haven, CT 06519-1754
2
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.
3
Anton Limo
East Haven, CT, New Haven, CT 06513
Anton Limo is an elite limo transport company offering fully licensed vehicles and first-class services that meets your widest satisfaction. Whether you need a luxury limo for a special occasion, an appointment or a trip; we reserved the best services to secure your broad needs 24/7. We offer exclusive service on airport transfers:Our pricing is very affordable and we are located in Connecticut.
4
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.
5
BrainXcape
160 Broadway 3rd Fl, New York City, NY 10038
6
Philadelphia Distilling
25 E Allen St, Philadelphia, PA 19123-1753
7
Old City Hall
Independence Mall, Philadelphia, PA 19106
8
Cylburn Arboretum
4915 Greenspring Ave, Baltimore, MD 21209-4698
9
Howard Peters Rawlings Conservatory and Botanic Gardens of Baltimore
3100 Swann Dr Druid Hill Park, Baltimore, MD 21217
10
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.
11
Regal River City Marketplace Stadium 14
12884 City Center Blvd River City Marketplace, Jacksonville, FL 32218-7216
12
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.
13
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.
14
Young's Paso Fino Ranch
7950 NW 80th Ave, Ocala, FL 34482-1112
15
Marion Theatre
50 S Magnolia Ave, Ocala, FL 34471-1153
16
Ocala Palms Golf & Country Club
5174 NW 26th St, Ocala, FL 34482-3250
17
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!
18
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.
19
The Legends Walk Course
8505 W Irlo Bronson Memorial Hwy Orange Lake Resort, Kissimmee, FL 34747-8217
20
Corpus Christi Catholic Church
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
21
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.
Customize this Trip

OVERVIEW

1
Start:New Haven Railroad Station
New Haven, Connecticut·
4.0
(97) review
50 Union Ave, New Haven, CT 06519-1754
2
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
3
Anton Limo
New Haven, Connecticut·
5.0
(9) review
Anton Limo is an elite limo transport company offering fully licensed vehicles and first-class services that meets your widest satisfaction. Whether you need a luxury limo for a special occasion, an appointment or a trip; we reserved the best services to secure your broad needs 24/7. We offer exclusive service on airport transfers:Our pricing is very affordable and we are located in Connecticut.
East Haven, CT, New Haven, CT 06513
4
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
5
BrainXcape
New York City, New York·
5.0
(99) review
160 Broadway 3rd Fl, New York City, NY 10038
6
Philadelphia Distilling
Philadelphia, Pennsylvania·
5.0
(98) review
25 E Allen St, Philadelphia, PA 19123-1753
7
Old City Hall
Philadelphia, Pennsylvania·
4.5
(99) review
Independence Mall, Philadelphia, PA 19106
8
Cylburn Arboretum
Baltimore, Maryland·
4.5
(91) review
4915 Greenspring Ave, Baltimore, MD 21209-4698
9
Howard Peters Rawlings Conservatory and Botanic Gardens of Baltimore
Baltimore, Maryland·
4.5
(99) review
3100 Swann Dr Druid Hill Park, Baltimore, MD 21217
10
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
11
Regal River City Marketplace Stadium 14
Jacksonville, Florida·
4.5
(9) review
12884 City Center Blvd River City Marketplace, Jacksonville, FL 32218-7216
12
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
13
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
14
Young's Paso Fino Ranch
Ocala, Florida·
4.0
(9) review
7950 NW 80th Ave, Ocala, FL 34482-1112
15
Marion Theatre
Ocala, Florida·
4.5
(90) review
50 S Magnolia Ave, Ocala, FL 34471-1153
16
Ocala Palms Golf & Country Club
Ocala, Florida·
4.5
(9) review
5174 NW 26th St, Ocala, FL 34482-3250
17
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
18
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
19
The Legends Walk Course
Kissimmee, Florida·
4.0
(96) review
8505 W Irlo Bronson Memorial Hwy Orange Lake Resort, Kissimmee, FL 34747-8217
20
Corpus Christi Catholic Church
Celebration, Orlando, Florida·
5.0
(99) review
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
21
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

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Bridgeport and Leesburg?
The distance is 1,138 miles
What's the travel time between Bridgeport and Leesburg?
The driving time can vary depending on traffic conditions, but it is typically 21h 54m mins in normal traffic
What are some of the best cities to visit between Bridgeport and Leesburg?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Leesburg?
There are plenty! Here are some stops you shouldn’t miss on your way to Leesburg
What’s the weather like in Leesburg?
The weather in Leesburg is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Leesburg in January
Weather in Leesburg in February
Weather in Leesburg in March
Weather in Leesburg in April
Weather in Leesburg in May
Weather in Leesburg in June
Weather in Leesburg in July
Weather in Leesburg in August
Weather in Leesburg in September
Weather in Leesburg in October
Weather in Leesburg in November
Weather in Leesburg in December
Interested in a detailed plan for your time in Leesburg?
Plan your dream Leesburg trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Leesburg
A 2-day itinerary in Leesburg
A 3-day itinerary in Leesburg
A 4-day itinerary in Leesburg
A 5-day itinerary in Leesburg
A 6-day itinerary in Leesburg
Where else can I travel to if I'm starting my trip in Bridgeport?
We have a lot of great trip options for Bridgeport! See the links below for all the itineraries we created for you