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By Huuk Team

Road trip from Madison to Poughkeepsie

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ITINERARY

17h 58m960 miles16 stops
1
First Unitarian Meeting House of Madison
900 University Bay Dr, Madison, WI 53705-2298
2
Alliant Energy Center
1919 Alliant Energy Center Way, Madison, WI 53713-1400
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!
3
Arista Spa & Salon
2155 City Gate Ln Ste 201, Naperville, IL 60563-7703
Arista Spa & Salon in Naperville, Illinois has been artfully designed with attention to the finest details to soothe the body and enrich the soul. In this special place we bring together ancient Mediterranean healing with modern innovation, cherished rituals for cleansing and wellness with the best science has to offer your skin, hair and body. All in inspiring surroundings with a staff that is both nurturing and world class. The Arista Spa & Salon and its services have been crafted to meet the needs of both men and women. You may also enjoy our inspiring couples' room, allowing you to experience complete relaxation with someone special.
4
Wrigley Field
1060 W. Addison St., Chicago, IL 60613-4566
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.
5
Boystown
Chicago, IL
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
6
Michigan Avenue Bridge
333 Michigan Ave, Chicago, IL 60601-3901
The view from the bridge is one of the best vistas the city has to offer.
7
Allen County War Memorial Coliseum
4000 Parnell Ave, Fort Wayne, IN 46805-1414
8
Lakeside Park & Rose Garden
1401 Lake Ave, Fort Wayne, IN 46805
9
Sprucewood Shores Estate Winery
7258 Cty Rd, 50 West, Harrow, Essex, Ontario N0R 1G0 Canada
The Sprucewood Family warmly welcomes you to sample handcrafted 100% Ontario VQA wines at Ontario's only beachfront destination vineyard, winery and tasting room. We are situated on 45 Acres with access to gardens, a sandy beach, and picnic tables. Enjoy a glass of wine with a picnic basket and explore our grounds year round. Tasting room open 7 days a week 11am - 5pm (we occasionally close early due to special events. Please check our social media for daily updates @sprucewoodshores)
10
Rock & Roll Hall of Fame
1100 Rock and Roll Blvd Main Terminal, Cleveland, OH 44114-1023
Headquartered in a boldly designed building on Lake Erie's shore, The Rock and Roll Hall of Fame is a 150,000-square-foot museum featuring ever-changing exhibits documenting the history of rock and roll, from Elvis to our days. You’ll see hundreds of original artifacts, from Jimi Hendrix outfits to The Beatles’ handwritten lyrics. Experience the excitement of a Rock Hall induction night at the Power of Rock Experience or have your very own jam session at the Garage. You can also watch a concert while you're here, so check out the Rock Hall’s schedule and plan ahead. – Tripadvisor
11
Federal Reserve Bank of Cleveland: Education and Learning Center
1455 E 6th St, Cleveland, OH 44114-2517
Ever wonder how money works or what the Federal Reserve Bank of Cleveland does as part of the central bank of the US? Visit our Education and Learning Center featuring more than 25 fun, hands-on exhibits that answer these questions and more! We have interactive games, visual exhibits, creative stations, and illuminating films that explain everything about money you can think of, from how we use it, to why it looks the way it looks. Come see our historic lobby, take pictures with our money tree, trade coconuts on Barter Island, identify counterfeit bills, and even make your own money! All this in the heart of Cleveland, just steps away from downtown attractions. Admission is free and photos are welcome.
12
Lock 3
200 S Main St, Akron, OH 44308-1315
13
Paladin Brewing
6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012
14
Hollywood Gaming Mahoning Valley Race Course
655 N Canfield Niles Rd, Youngstown, OH 44515-1102
15
ScareHouse
461 Pittsburgh Mills Cir, Pittsburgh, PA 15084-3833
Pittsburgh Zombies love shopping malls – and we think you will love our NEW, larger, and permanent home inside the Galleria at Pittsburgh Mills. Thank You Pittsburgh for supporting us for more than 20 years of fears! ScareHouse has been ranked as one of “America’s Scariest Halloween Attractions” by Travel Channel and has been featured on Good Morning America, USA TODAY, The Daily Show and many other national media outlets.
16
Steamtown National Historic Site
350 Cliff St, Scranton, PA 18503
This small museum is all about steam engines and their contribution to America's economy in the 19th century.
Customize this Trip

OVERVIEW

1
Start:First Unitarian Meeting House of Madison
Madison, Wisconsin·
4.5
(96) review
900 University Bay Dr, Madison, WI 53705-2298
2
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!
1919 Alliant Energy Center Way, Madison, WI 53713-1400
3
Arista Spa & Salon
Naperville, DuPage County, Illinois·
4.0
(9) review
Arista Spa & Salon in Naperville, Illinois has been artfully designed with attention to the finest details to soothe the body and enrich the soul. In this special place we bring together ancient Mediterranean healing with modern innovation, cherished rituals for cleansing and wellness with the best science has to offer your skin, hair and body. All in inspiring surroundings with a staff that is both nurturing and world class. The Arista Spa & Salon and its services have been crafted to meet the needs of both men and women. You may also enjoy our inspiring couples' room, allowing you to experience complete relaxation with someone special.
2155 City Gate Ln Ste 201, Naperville, IL 60563-7703
4
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.
1060 W. Addison St., Chicago, IL 60613-4566
5
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
Chicago, IL
6
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.
333 Michigan Ave, Chicago, IL 60601-3901
7
Allen County War Memorial Coliseum
Fort Wayne, Indiana·
4.0
(99) review
4000 Parnell Ave, Fort Wayne, IN 46805-1414
8
Lakeside Park & Rose Garden
Fort Wayne, Indiana·
4.5
(96) review
1401 Lake Ave, Fort Wayne, IN 46805
9
Sprucewood Shores Estate Winery
Harrow, Essex, Ontario·
4.5
(97) review
The Sprucewood Family warmly welcomes you to sample handcrafted 100% Ontario VQA wines at Ontario's only beachfront destination vineyard, winery and tasting room. We are situated on 45 Acres with access to gardens, a sandy beach, and picnic tables. Enjoy a glass of wine with a picnic basket and explore our grounds year round. Tasting room open 7 days a week 11am - 5pm (we occasionally close early due to special events. Please check our social media for daily updates @sprucewoodshores)
7258 Cty Rd, 50 West, Harrow, Essex, Ontario N0R 1G0 Canada
10
Rock & Roll Hall of Fame
Cleveland, Ohio·
4.5
(9964) review
Headquartered in a boldly designed building on Lake Erie's shore, The Rock and Roll Hall of Fame is a 150,000-square-foot museum featuring ever-changing exhibits documenting the history of rock and roll, from Elvis to our days. You’ll see hundreds of original artifacts, from Jimi Hendrix outfits to The Beatles’ handwritten lyrics. Experience the excitement of a Rock Hall induction night at the Power of Rock Experience or have your very own jam session at the Garage. You can also watch a concert while you're here, so check out the Rock Hall’s schedule and plan ahead. – Tripadvisor
1100 Rock and Roll Blvd Main Terminal, Cleveland, OH 44114-1023
11
Federal Reserve Bank of Cleveland: Education and Learning Center
Cleveland, Ohio·
4.5
(95) review
Ever wonder how money works or what the Federal Reserve Bank of Cleveland does as part of the central bank of the US? Visit our Education and Learning Center featuring more than 25 fun, hands-on exhibits that answer these questions and more! We have interactive games, visual exhibits, creative stations, and illuminating films that explain everything about money you can think of, from how we use it, to why it looks the way it looks. Come see our historic lobby, take pictures with our money tree, trade coconuts on Barter Island, identify counterfeit bills, and even make your own money! All this in the heart of Cleveland, just steps away from downtown attractions. Admission is free and photos are welcome.
1455 E 6th St, Cleveland, OH 44114-2517
12
Lock 3
Akron, Ohio·
4.5
(98) review
200 S Main St, Akron, OH 44308-1315
13
Paladin Brewing
Austintown, Youngstown, Ohio·
4.5
(9) review
6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012
14
Hollywood Gaming Mahoning Valley Race Course
Youngstown, Ohio·
3.5
(83) review
655 N Canfield Niles Rd, Youngstown, OH 44515-1102
15
ScareHouse
Pittsburgh, Pennsylvania·
4.0
(87) review
Pittsburgh Zombies love shopping malls – and we think you will love our NEW, larger, and permanent home inside the Galleria at Pittsburgh Mills. Thank You Pittsburgh for supporting us for more than 20 years of fears! ScareHouse has been ranked as one of “America’s Scariest Halloween Attractions” by Travel Channel and has been featured on Good Morning America, USA TODAY, The Daily Show and many other national media outlets.
461 Pittsburgh Mills Cir, Pittsburgh, PA 15084-3833
16
Steamtown National Historic Site
Scranton, Pennsylvania·
4.5
(902) review
This small museum is all about steam engines and their contribution to America's economy in the 19th century.
350 Cliff St, Scranton, PA 18503

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Madison and Poughkeepsie?
The distance is 960 miles
What's the travel time between Madison and Poughkeepsie?
The driving time can vary depending on traffic conditions, but it is typically 17h 58m mins in normal traffic
What are some of the best cities to visit between Madison and Poughkeepsie?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Poughkeepsie?
There are plenty! Here are some stops you shouldn’t miss on your way to Poughkeepsie
What’s the weather like in Poughkeepsie?
The weather in Poughkeepsie is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Poughkeepsie in January
Weather in Poughkeepsie in February
Weather in Poughkeepsie in March
Weather in Poughkeepsie in April
Weather in Poughkeepsie in May
Weather in Poughkeepsie in June
Weather in Poughkeepsie in July
Weather in Poughkeepsie in August
Weather in Poughkeepsie in September
Weather in Poughkeepsie in October
Weather in Poughkeepsie in November
Weather in Poughkeepsie in December
Interested in a detailed plan for your time in Poughkeepsie?
Plan your dream Poughkeepsie trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Poughkeepsie
A 2-day itinerary in Poughkeepsie
A 3-day itinerary in Poughkeepsie
A 4-day itinerary in Poughkeepsie
A 5-day itinerary in Poughkeepsie
A 6-day itinerary in Poughkeepsie
Where else can I travel to if I'm starting my trip in Madison?
We have a lot of great trip options for Madison! See the links below for all the itineraries we created for you