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By Huuk Team

Road trip from Poughkeepsie to Enterprise

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iconConcerts & Shows
iconMuseums
iconOutdoor Activities
iconFun & Games
iconFood & Drink
iconSpas & Wellness
iconSights & Landmarks
Show more (4+)

ITINERARY

45h 25m2,562 miles18 stops
1
The Rat Pack is Back
255 E Flamingo Rd Tuscany Suites and Casino, Las Vegas, NV 89169-4708
The number 1 Rat Pack show in the world, now in its' 24th year. The only show of its' kind with an award from the Congress of the United States of America, a full time show running in Las Vegas and national and international touring companies, appearances in over 40 states, 8000 performances and over 3 million satisfied customers.
2
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.
3
Hollywood Gaming Mahoning Valley Race Course
655 N Canfield Niles Rd, Youngstown, OH 44515-1102
4
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
5
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.
6
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
7
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.
8
Quad Cities Symphony Orchestra
327 Brady St, Davenport, IA 52801-1508
9
Endless Brews
310 N Main St, Davenport, IA 52801-1410
We are a bottle shop & craft beer bar with 20 taps and over 300 select bottles and cans for carry-out.
10
German American Heritage Center
712 W 2nd St, Davenport, IA 52802-1410
11
Hot Shops Art Center
13th & Nicholas, Omaha, NE 68102
12
Hollywood Candy
1209 Jackson St Omaha, NE, Omaha, NE 68102-2826
Hollywood Candy is a giant candy store proudly serving Omaha’s Old Market since 2007. We offer a large selection of housemate chocolate candy including our chocolate covered bacon, chocolate potato chips, candy cookie pops and our famous Peanut Butter Surprise. We have all flavors or Jelly Belly jelly beans and a large selection of M&M’s. We offer the largest selection of bulk candy in the area including hard to find retro brands, favorite brands like Hershey’s and Oreo, rock candy, gummies, sour candy, and lollipops. Our Soda Shoppe offers over 200 varieties of familiar and unique soda brands. We have the largest collection of PEZ dispensers for everyone to enjoy plus a large assortment for sale.
13
LoDo Massage Studio
3101 Walnut St Ste 200, Denver, CO 80205-2330
Therapeutic Massage Services! At LoDo Massage Studio, we believe a good massage can be a powerful tool to reshape and restore how your body feels and functions. Our massage therapists are talented, licensed, experts who are passionate about providing transformational therapeutic bodywork. Our studio encourages our LMTs to use their unique experience and skill to customize your massage to your body’s exact needs by using a wide range of modalities. Looking for a place to start? Named for our beloved city, our signature Mile High Massage service is tailored to suit you just right. You could also choose a relaxing Swedish massage, invigorating Sports Massage, or effective Neuromuscular Massage. We also offer add-ons like Aromatherapy, and Hot Towels to create a massage bespoke for your body.
14
Paladin Brewing
6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012
15
Lock 3
200 S Main St, Akron, OH 44308-1315
16
Allen County War Memorial Coliseum
4000 Parnell Ave, Fort Wayne, IN 46805-1414
17
Fitness Sports
8810 Swanson Blvd, Des Moines, IA 50325-6910
Iowa's first Specialty Running & Walking store with a emphasis on personal service. Ou r stone motto is "Where You have the Right to B-Fit". Est. in 1984.
18
Fun Plex
7003 Q St, Omaha, NE 68117-1649
Customize this Trip

OVERVIEW

1
Start:The Rat Pack is Back
Las Vegas, Nevada·
4.0
(999) review
The number 1 Rat Pack show in the world, now in its' 24th year. The only show of its' kind with an award from the Congress of the United States of America, a full time show running in Las Vegas and national and international touring companies, appearances in over 40 states, 8000 performances and over 3 million satisfied customers.
255 E Flamingo Rd Tuscany Suites and Casino, Las Vegas, NV 89169-4708
2
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
3
Hollywood Gaming Mahoning Valley Race Course
Youngstown, Ohio·
3.5
(83) review
655 N Canfield Niles Rd, Youngstown, OH 44515-1102
4
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
5
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
6
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
7
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
8
Quad Cities Symphony Orchestra
Davenport, Iowa·
4.5
(8) review
327 Brady St, Davenport, IA 52801-1508
9
Endless Brews
Davenport, Iowa·
4.5
(9) review
We are a bottle shop & craft beer bar with 20 taps and over 300 select bottles and cans for carry-out.
310 N Main St, Davenport, IA 52801-1410
10
German American Heritage Center
Davenport, Iowa·
4.5
(84) review
712 W 2nd St, Davenport, IA 52802-1410
11
Hot Shops Art Center
Omaha, Nebraska·
4.5
(96) review
13th & Nicholas, Omaha, NE 68102
12
Hollywood Candy
Omaha, Nebraska·
4.0
(99) review
Hollywood Candy is a giant candy store proudly serving Omaha’s Old Market since 2007. We offer a large selection of housemate chocolate candy including our chocolate covered bacon, chocolate potato chips, candy cookie pops and our famous Peanut Butter Surprise. We have all flavors or Jelly Belly jelly beans and a large selection of M&M’s. We offer the largest selection of bulk candy in the area including hard to find retro brands, favorite brands like Hershey’s and Oreo, rock candy, gummies, sour candy, and lollipops. Our Soda Shoppe offers over 200 varieties of familiar and unique soda brands. We have the largest collection of PEZ dispensers for everyone to enjoy plus a large assortment for sale.
1209 Jackson St Omaha, NE, Omaha, NE 68102-2826
13
LoDo Massage Studio
Denver, Colorado·
5.0
(99) review
Therapeutic Massage Services! At LoDo Massage Studio, we believe a good massage can be a powerful tool to reshape and restore how your body feels and functions. Our massage therapists are talented, licensed, experts who are passionate about providing transformational therapeutic bodywork. Our studio encourages our LMTs to use their unique experience and skill to customize your massage to your body’s exact needs by using a wide range of modalities. Looking for a place to start? Named for our beloved city, our signature Mile High Massage service is tailored to suit you just right. You could also choose a relaxing Swedish massage, invigorating Sports Massage, or effective Neuromuscular Massage. We also offer add-ons like Aromatherapy, and Hot Towels to create a massage bespoke for your body.
3101 Walnut St Ste 200, Denver, CO 80205-2330
14
Paladin Brewing
Austintown, Youngstown, Ohio·
4.5
(9) review
6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012
15
Lock 3
Akron, Ohio·
4.5
(98) review
200 S Main St, Akron, OH 44308-1315
16
Allen County War Memorial Coliseum
Fort Wayne, Indiana·
4.0
(99) review
4000 Parnell Ave, Fort Wayne, IN 46805-1414
17
Fitness Sports
Des Moines, Iowa·
5.0
(9) review
Iowa's first Specialty Running & Walking store with a emphasis on personal service. Ou r stone motto is "Where You have the Right to B-Fit". Est. in 1984.
8810 Swanson Blvd, Des Moines, IA 50325-6910
18
Fun Plex
Omaha, Nebraska·
3.5
(92) review
7003 Q St, Omaha, NE 68117-1649

CHECKLIST

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Hand sanitizer and wet wipes
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Driver’s license and vehicle registration
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FAQ
Frequently Asked Questions
What's the driving distance between Poughkeepsie and Enterprise?
The distance is 2,562 miles
What's the travel time between Poughkeepsie and Enterprise?
The driving time can vary depending on traffic conditions, but it is typically 45h 25m mins in normal traffic
What are some of the best cities to visit between Poughkeepsie and Enterprise?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Enterprise?
There are plenty! Here are some stops you shouldn’t miss on your way to Enterprise
What’s the weather like in Enterprise?
The weather in Enterprise is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Enterprise in January
Weather in Enterprise in February
Weather in Enterprise in March
Weather in Enterprise in April
Weather in Enterprise in May
Weather in Enterprise in June
Weather in Enterprise in July
Weather in Enterprise in August
Weather in Enterprise in September
Weather in Enterprise in October
Weather in Enterprise in November
Weather in Enterprise in December
Interested in a detailed plan for your time in Enterprise?
Plan your dream Enterprise trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Enterprise
A 2-day itinerary in Enterprise
A 3-day itinerary in Enterprise
A 4-day itinerary in Enterprise
A 5-day itinerary in Enterprise
A 6-day itinerary in Enterprise
Where else can I travel to if I'm starting my trip in Poughkeepsie?
We have a lot of great trip options for Poughkeepsie! See the links below for all the itineraries we created for you