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By Huuk Team

Road trip from Chicago to Oyster Bay

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ITINERARY

15h 24m822 miles18 stops
1
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.
2
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
3
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.
4
Allen County War Memorial Coliseum
4000 Parnell Ave, Fort Wayne, IN 46805-1414
5
Lakeside Park & Rose Garden
1401 Lake Ave, Fort Wayne, IN 46805
6
Amherstburg Navy Yard National Historic Site
Dalhousie Street, Amherstburg, Ontario N9V 1W7 Canada
7
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)
8
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
9
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.
10
Museum of Contemporary Art Cleveland
11400 Euclid Ave, Cleveland, OH 44106-3926
11
Lock 3
200 S Main St, Akron, OH 44308-1315
12
Paladin Brewing
6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012
13
Hollywood Gaming Mahoning Valley Race Course
655 N Canfield Niles Rd, Youngstown, OH 44515-1102
14
Basilica of Our Lady of Mount Carmel
343 Via Mount Carmel Ave, Youngstown, OH 44505-3037
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
BrainXcape
160 Broadway 3rd Fl, New York City, NY 10038
17
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.
18
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.
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OVERVIEW

Our boat trip to Oyster Bay will be one that you'll never forget! We'll embark on a grand adventure, starting from the bustling city of Chicago which is located on the shores of Lake Michigan. As we bid farewell to the towering skyscrapers and vibrant streets, our journey will take us across the vast expanse of the Great Lakes, where we'll sail along the picturesque shorelines of various states. Along the way, we'll have the opportunity to witness stunning sunsets over the tranquil waters and gaze up at the starlit sky as we navigate our course.

As we approach the eastern end of Lake Erie, we'll enter the legendary Erie Canal, a historic waterway that played a pivotal role in the development of the United States. Traversing through the picturesque countryside, we'll marvel at the engineering marvel of the canal's locks, which gently lift and lower our boat, allowing us to continue our journey. Emerging from the canal, we'll find ourselves in the majestic Hudson River, a waterway that has borne witness to centuries of history. As we sail along its serene waters, we'll pass by towering cliffs, lush forests, and quaint towns, each with their own unique charm and stories to tell.

Finally, our adventure culminates as we arrive at the serene Oyster Bay, a place steeped in maritime heritage and surrounded by natural beauty. Throughout our journey, we'll have the chance to learn about the rich history and diverse cultures that define the regions we pass through. Whether you're an avid history buff, a nature enthusiast, or simply seeking an unforgettable experience, this boat trip promises to create lasting memories that will be cherished for a lifetime.

1
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.
333 Michigan Ave, Chicago, IL 60601-3901
2
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
3
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
4
Allen County War Memorial Coliseum
Fort Wayne, Indiana·
4.0
(99) review
4000 Parnell Ave, Fort Wayne, IN 46805-1414
5
Lakeside Park & Rose Garden
Fort Wayne, Indiana·
4.5
(96) review
1401 Lake Ave, Fort Wayne, IN 46805
6
Amherstburg Navy Yard National Historic Site
Amherstburg, Ontario·
5.0
(94) review
Dalhousie Street, Amherstburg, Ontario N9V 1W7 Canada
7
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
8
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
9
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
10
Museum of Contemporary Art Cleveland
Cleveland, Ohio·
3.5
(93) review
11400 Euclid Ave, Cleveland, OH 44106-3926
11
Lock 3
Akron, Ohio·
4.5
(98) review
200 S Main St, Akron, OH 44308-1315
12
Paladin Brewing
Austintown, Youngstown, Ohio·
4.5
(9) review
6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012
13
Hollywood Gaming Mahoning Valley Race Course
Youngstown, Ohio·
3.5
(83) review
655 N Canfield Niles Rd, Youngstown, OH 44515-1102
14
Basilica of Our Lady of Mount Carmel
Youngstown, Ohio·
4.5
(7) review
343 Via Mount Carmel Ave, Youngstown, OH 44505-3037
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
BrainXcape
New York City, New York·
5.0
(99) review
160 Broadway 3rd Fl, New York City, NY 10038
17
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
18
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

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Oyster Bay?
The distance is 822 miles
What's the travel time between Chicago and Oyster Bay?
The driving time can vary depending on traffic conditions, but it is typically 15h 24m mins in normal traffic
What are some of the best cities to visit between Chicago and Oyster Bay?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Oyster Bay?
There are plenty! Here are some stops you shouldn’t miss on your way to Oyster Bay
What’s the weather like in Oyster Bay?
The weather in Oyster Bay is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Oyster Bay in January
Weather in Oyster Bay in February
Weather in Oyster Bay in March
Weather in Oyster Bay in April
Weather in Oyster Bay in May
Weather in Oyster Bay in June
Weather in Oyster Bay in July
Weather in Oyster Bay in August
Weather in Oyster Bay in September
Weather in Oyster Bay in October
Weather in Oyster Bay in November
Weather in Oyster Bay in December
Interested in a detailed plan for your time in Oyster Bay?
Plan your dream Oyster Bay trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Oyster Bay
A 2-day itinerary in Oyster Bay
A 3-day itinerary in Oyster Bay
A 4-day itinerary in Oyster Bay
A 5-day itinerary in Oyster Bay
A 6-day itinerary in Oyster Bay
Where else can I travel to if I'm starting my trip in Chicago?
We have a lot of great trip options for Chicago! See the links below for all the itineraries we created for you