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Road trip from New York to Madison
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Boat Tours & Water Sports
Fun & Games
Nightlife
Food & Drink
Shopping
Nature & Parks
MuseumsShow more (4+)
All Category
Boat Tours & Water SportsFun & GamesNightlifeFood & DrinkShoppingNature & ParksMuseums
Sights & Landmarks
Events
Spas & WellnessReset
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ITINERARY
17h 57m945 miles22 stops
1
BrainXcape
2
The Blue Bar, Algonquin Hotel
Comfortable and classic, the lounge of the Algonquin Hotel is a New York landmark.
3
Hollywood Gaming Mahoning Valley Race Course
4
Paladin Brewing
5
Sheiban Jewelers
As Cleveland, Ohio's premiere jewelry store, Sheiban Jewelers provides custom made jewelry and top luxury swiss watch and jewelry brands to highlight life’s milestones. Sheiban Jewelers is proud to be an Official Rolex Jeweler in the Cleveland, Ohio area and offers luxury engagement rings, jewelry, and watches from brands including Verragio, Tacori, Tudor, Omega, Breitling, Montblanc, and more.
6
Mill Stream Run Reservation
7
National Shrine of St Jude
8
Promontory Point
9
Spring Awakening Music Festival
10
A. Philip Randolph Pullman Porter Museum
The National APR Pullman Porter Museum, is located in the National Park Service-Pullman National Monument. It is the only one of its kind world-wide. NAPRPPM is the first Black Labor History museum, in the United States, that exclusively tells the story of the Pullman Porters, The Brotherhood of Sleeping Car Porters labor union, and A. Philip Randolph Its founder. Tucked away on a quiet corner at the north end of Pullman National monument, don’t let the unassuming exterior keep you from missing this black heritage treasure. The museum presents, and interprets content intended to educate the public-on the impact the union had on organized labor, and on America’s modern day civil rights movement The exhibits chronicle the formation of the Brotherhood of Sleeping Car Porters; the first Black labor union in the United States chartered under the American Federation of Labor. Exhibits depict important activities on their amazing JOURNEY OF UNITY that ended in victory.
11
Soldier Field
Venerable home field of the Chicago Bears football team.
12
Michigan Avenue Bridge
The view from the bridge is one of the best vistas the city has to offer.
13
Boystown
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
14
Wrigley Field
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
15
Gompers Park
16
BATL Axe Throwing
At BATL Axe Throwing, we believe that sport should be inclusive, fun for everyone in the family, and above all, be a safe entertainment bullseye. With safety and teaching being the highest priority at BATL, our coaches help everyone over twelve years old remember the feeling of their first bullseye. Whether you're bringing your young family out for some in-town entertainment or putting on a stag, bachelorette, birthday, team-building, or fundraising event, we'll make sure it's memorable and safe. No matter what BATL location you visit across North America, you can expect delicious food and drinks, axe throwing lanes, expert coaching, and a fun tournament. Easy online booking in less than 3 minutes and group discounts are always available on our website.
17
Legendary Private Car
First class transportation for any occasion - from airport car service to luxury Chicago limo service for a special occasion | Legendary Private Car Chicago Services: Black Car Service Chicago Chicago Car Service Limo Service Chicago Car Service to O'Hare Car Service to Midway
18
Aldo Leopold Nature Center
19
The Tasting Room
20
KOSA Spa
KOSA Spa provides a sanctuary; a place to retreat, to nourish body, mind, and spirit, and in so doing reconnect with one’s best self. KOSA Spa blends wellness best practices from the 5,000-year-old Indian tradition of Ayurveda with seasonal, organic, Wisconsin-sourced ingredients and artisanal products. KOSA Spa’s offerings include customized wellness balancing plans; treatments, including Abhyanga, Shirodhara, Pinda Sweda, Massage, and Facials; and personal retreats that include access to our hot-stone sauna, aromatherapy hydro-steam room, meditation studio, sanctuary lounge, and organic, Ayurvedic teas and foods.
21
Alliant Energy Center
Our premier downtown multi-venue complex features four unique and versatile venues: Veterans Memorial Coliseum, Exhibition Hall, the New Holland Pavilions, and Willow Island. A top choice for expositions, conventions, meetings, concerts, sporting events, ag events, and much more, the Alliant Energy Center complex is a one-stop-shop for all your events. Ample parking, mouthwatering catering, dedicated staff, and a full range of rental equipment & high speed internet make AEC an event planners delight!
22
First Unitarian Meeting House of Madison
Customize this Trip
OVERVIEW
Escape the hustle and bustle of the Big Apple and embark on a scenic journey through the picturesque landscapes of New York and Connecticut, culminating in the vibrant university town of Madison, Wisconsin. This leisurely adventure invites you to unwind as you traverse rolling hills, charming small towns, and tranquil waterways.
Experience the transition from the bustling streets of Manhattan to the serene shores of Long Island Sound. Marvel at the iconic landmarks of New York City as you depart, then savor the tranquility of coastal drives and quaint New England villages. Immerse yourself in the rich history and cultural heritage of the region, visiting historic sites and discovering hidden gems along the way.
As you approach Madison, the landscape transforms into a vibrant tapestry of lakes, forests, and rolling hills. Embrace the youthful energy of the university town, exploring its vibrant arts scene, delectable dining options, and outdoor recreation opportunities. Lose yourself in the charm of the Midwest as you immerse yourself in the friendly atmosphere and picturesque surroundings of Madison.
1
Start:BrainXcape
New York City, New York·
5.0
(99) review
160 Broadway 3rd Fl, New York City, NY 10038
2
Start: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.
3
Start:Hollywood Gaming Mahoning Valley Race Course
Youngstown, Ohio·
3.5
(83) review
655 N Canfield Niles Rd, Youngstown, OH 44515-1102
4
Start:Paladin Brewing
Austintown, Youngstown, Ohio·
4.5
(9) review
6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012
5
Start:Sheiban Jewelers
Cleveland, Ohio·
(0) review
As Cleveland, Ohio's premiere jewelry store, Sheiban Jewelers provides custom made jewelry and top luxury swiss watch and jewelry brands to highlight life’s milestones. Sheiban Jewelers is proud to be an Official Rolex Jeweler in the Cleveland, Ohio area and offers luxury engagement rings, jewelry, and watches from brands including Verragio, Tacori, Tudor, Omega, Breitling, Montblanc, and more.
6
Start:Mill Stream Run Reservation
Cleveland, Ohio·
4.5
(33) review
9485 Eastland Rd, Cleveland, OH 44149-1418
7
Start:National Shrine of St Jude
Chicago, Illinois·
4.5
(7) review
3200 E 91st St, Chicago, IL 60617-4408
8
Start:Promontory Point
Chicago, Illinois·
5.0
(9) review
5491 S Shore Dr, Chicago, IL 60615-5983
9
Start:Spring Awakening Music Festival
Chicago, Illinois·
4.0
(8) review
6401 S Stony Island Ave Jackson Park, Chicago, IL 60637-3800
10
Start:A. Philip Randolph Pullman Porter Museum
Chicago, Illinois·
3.5
(7) review
The National APR Pullman Porter Museum, is located in the National Park Service-Pullman National Monument. It is the only one of its kind world-wide. NAPRPPM is the first Black Labor History museum, in the United States, that exclusively tells the story of the Pullman Porters, The Brotherhood of Sleeping Car Porters labor union, and A. Philip Randolph Its founder. Tucked away on a quiet corner at the north end of Pullman National monument, don’t let the unassuming exterior keep you from missing this black heritage treasure. The museum presents, and interprets content intended to educate the public-on the impact the union had on organized labor, and on America’s modern day civil rights movement The exhibits chronicle the formation of the Brotherhood of Sleeping Car Porters; the first Black labor union in the United States chartered under the American Federation of Labor. Exhibits depict important activities on their amazing JOURNEY OF UNITY that ended in victory.
11
Start:Soldier Field
Chicago, Illinois·
4.0
(935) review
Venerable home field of the Chicago Bears football team.
12
Start:Michigan Avenue Bridge
Chicago, Illinois·
4.5
(985) review
The view from the bridge is one of the best vistas the city has to offer.
13
Start:Boystown
Chicago, Illinois·
4.5
(98) review
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
14
Start:Wrigley Field
Chicago, Illinois·
4.5
(9953) review
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
15
Start:Gompers Park
Chicago, Illinois·
4.0
(5) review
4222 W Foster Ave, Chicago, IL 60630-2718
16
Start:BATL Axe Throwing
Chicago, Illinois·
5.0
(450) review
At BATL Axe Throwing, we believe that sport should be inclusive, fun for everyone in the family, and above all, be a safe entertainment bullseye. With safety and teaching being the highest priority at BATL, our coaches help everyone over twelve years old remember the feeling of their first bullseye. Whether you're bringing your young family out for some in-town entertainment or putting on a stag, bachelorette, birthday, team-building, or fundraising event, we'll make sure it's memorable and safe. No matter what BATL location you visit across North America, you can expect delicious food and drinks, axe throwing lanes, expert coaching, and a fun tournament. Easy online booking in less than 3 minutes and group discounts are always available on our website.
17
Start:Legendary Private Car
Chicago, Illinois·
5.0
(62) review
First class transportation for any occasion - from airport car service to luxury Chicago limo service for a special occasion | Legendary Private Car Chicago Services: Black Car Service Chicago Chicago Car Service Limo Service Chicago Car Service to O'Hare Car Service to Midway
18
Start:Aldo Leopold Nature Center
Monona, Madison, Wisconsin·
4.5
(44) review
330 Femrite Dr, Monona, Madison, WI 53716-3716
19
Start:The Tasting Room
Monona, Madison, Wisconsin·
4.5
(7) review
800 W Broadway Suite 100, Monona, Madison, WI 53713
20
Start:KOSA Spa
Madison, Wisconsin·
5.0
(9) review
KOSA Spa provides a sanctuary; a place to retreat, to nourish body, mind, and spirit, and in so doing reconnect with one’s best self. KOSA Spa blends wellness best practices from the 5,000-year-old Indian tradition of Ayurveda with seasonal, organic, Wisconsin-sourced ingredients and artisanal products. KOSA Spa’s offerings include customized wellness balancing plans; treatments, including Abhyanga, Shirodhara, Pinda Sweda, Massage, and Facials; and personal retreats that include access to our hot-stone sauna, aromatherapy hydro-steam room, meditation studio, sanctuary lounge, and organic, Ayurvedic teas and foods.
21
Start:Alliant Energy Center
Madison, Wisconsin·
4.0
(99) review
Our premier downtown multi-venue complex features four unique and versatile venues: Veterans Memorial Coliseum, Exhibition Hall, the New Holland Pavilions, and Willow Island. A top choice for expositions, conventions, meetings, concerts, sporting events, ag events, and much more, the Alliant Energy Center complex is a one-stop-shop for all your events. Ample parking, mouthwatering catering, dedicated staff, and a full range of rental equipment & high speed internet make AEC an event planners delight!
22
Start:First Unitarian Meeting House of Madison
Madison, Wisconsin·
4.5
(96) review
900 University Bay Dr, Madison, WI 53705-2298
CHECKLIST
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Frequently Asked Questions
What's the driving distance between New York and Madison?
The distance is 945 miles
What's the travel time between New York and Madison?
The driving time can vary depending on traffic conditions, but it is typically 17h 57m mins in normal traffic
What are some of the best cities to visit between New York and Madison?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Madison?
There are plenty! Here are some stops you shouldn’t miss on your way to Madison
What’s the weather like in Madison?
The weather in Madison is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Madison in January
Weather in Madison in February
Weather in Madison in March
Weather in Madison in April
Weather in Madison in May
Weather in Madison in June
Weather in Madison in July
Weather in Madison in August
Weather in Madison in September
Weather in Madison in October
Weather in Madison in November
Weather in Madison in December
Interested in a detailed plan for your time in Madison?
Plan your dream Madison trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Madison
A 2-day itinerary in Madison
A 3-day itinerary in Madison
A 4-day itinerary in Madison
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A 6-day itinerary in Madison
Where else can I travel to if I'm starting my trip in New York?
We have a lot of great trip options for New York! See the links below for all the itineraries we created for you
