Road trip from Boston to Enterprise
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Concerts & Shows
Museums
Outdoor Activities
Fun & Games
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Spas & Wellness
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All Category
Concerts & Shows
Museums
Outdoor Activities
Fun & Games
Food & Drink
Spas & Wellness
Sights & Landmarks
Water & Amusement Parks
Shopping
Nightlife
Nature & Parks
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ITINERARY
48h 59m2,740 miles25 stops
1
The Rat Pack is Back
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
Boston Public Garden
This Frederick Law Olmsted-designed park, famous for its Swan Boats, has over 600 varieties of trees and an ever-changing array of flowers. It is America's first public garden.
3
Boston Children's Museum
Highlights of this interactive museum include the "Science Playground," featuring giant soap bubble-making tools and the "New Balance Climb," which teaches kids the laws of physics while navigating through a two-story-high maze.
4
Hex: Old World Witchery
Salem Warlock Christian Day presents magical merchandise for both the curious and Witch alike. Whether you want a candle to bless your home, herbs and roots to make your own magic, a potion to attract love, the perfect ritual tool, a Voodoo doll made by a real practitioner, or to cast a spell at our authentic Witches' Altar, Hex is for those who believe in magic and those whose hearts beat with its fire.Be sure to visit our Witches' Altar of the Dead that stands at the Western wall of the shop. Here, countless visitors through the years have left messages, photos, and mementos in honor of departed loved ones in the spirit world. We welcome you to contribute to the magic!And, while there, have an authentic psychic reading with one of Salem's most talented Witches: Leanne Marrama, Laura Broderick, and Kyri Spencer!
5
Redemption Rock Brewing Co.
Redemption Rock Brewing Co. is a craft brewery, taproom, and cafe in Worcester, Mass. We make beer for people. "Beer for people" means beer enjoyed with a strong sense of community and camaraderie, and we aim to provide high-quality, fun beer in all its forms. Also, as a certified Benefit Corporation (B Corp), we’re dedicated to working for the community. It’s an essential part of our business, and we’re continually looking for new ways to support local organizations, partner with local businesses, and be a better kind of employer and corporate citizen. Finally, we’ve designed the Redemption Rock taproom to be the ultimate community gathering space. It’s bright, comfortable, and colorful and serves as both a coffeehouse and a bar. Visit us with your friends, come meet new friends, or even hold your private event here. We hope to see you soon.
6
DCU Center
7
Yale University Art Gallery
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.
8
New Haven Railroad Station
9
Steamtown National Historic Site
This small museum is all about steam engines and their contribution to America's economy in the 19th century.
10
Hollywood Gaming Mahoning Valley Race Course
11
Michigan Avenue Bridge
The view from the bridge is one of the best vistas the city has to offer.
12
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
13
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.
14
Quad Cities Symphony Orchestra
15
Endless Brews
We are a bottle shop & craft beer bar with 20 taps and over 300 select bottles and cans for carry-out.
16
German American Heritage Center
17
Hot Shops Art Center
18
Hollywood Candy
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.
19
LoDo Massage Studio
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.
20
Paladin Brewing
21
Lock 3
22
Rock & Roll Hall of Fame
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
23
Allen County War Memorial Coliseum
24
Fitness Sports
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.
25
Fun Plex
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.
2
Start:Boston Public Garden
Boston, Massachusetts·
4.5
(9979) review
This Frederick Law Olmsted-designed park, famous for its Swan Boats, has over 600 varieties of trees and an ever-changing array of flowers. It is America's first public garden.
3
Start:Boston Children's Museum
Boston, Massachusetts·
4.5
(994) review
Highlights of this interactive museum include the "Science Playground," featuring giant soap bubble-making tools and the "New Balance Climb," which teaches kids the laws of physics while navigating through a two-story-high maze.
4
Start:Hex: Old World Witchery
Salem, Massachusetts·
5.0
(1000) review
Salem Warlock Christian Day presents magical merchandise for both the curious and Witch alike. Whether you want a candle to bless your home, herbs and roots to make your own magic, a potion to attract love, the perfect ritual tool, a Voodoo doll made by a real practitioner, or to cast a spell at our authentic Witches' Altar, Hex is for those who believe in magic and those whose hearts beat with its fire.Be sure to visit our Witches' Altar of the Dead that stands at the Western wall of the shop. Here, countless visitors through the years have left messages, photos, and mementos in honor of departed loved ones in the spirit world. We welcome you to contribute to the magic!And, while there, have an authentic psychic reading with one of Salem's most talented Witches: Leanne Marrama, Laura Broderick, and Kyri Spencer!
5
Start:Redemption Rock Brewing Co.
Worcester, Massachusetts·
5.0
(9) review
Redemption Rock Brewing Co. is a craft brewery, taproom, and cafe in Worcester, Mass. We make beer for people. "Beer for people" means beer enjoyed with a strong sense of community and camaraderie, and we aim to provide high-quality, fun beer in all its forms. Also, as a certified Benefit Corporation (B Corp), we’re dedicated to working for the community. It’s an essential part of our business, and we’re continually looking for new ways to support local organizations, partner with local businesses, and be a better kind of employer and corporate citizen. Finally, we’ve designed the Redemption Rock taproom to be the ultimate community gathering space. It’s bright, comfortable, and colorful and serves as both a coffeehouse and a bar. Visit us with your friends, come meet new friends, or even hold your private event here. We hope to see you soon.
6
Start:DCU Center
Worcester, Massachusetts·
3.5
(93) review
50 Foster Street, Worcester, MA 01608-1305
7
Start: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.
8
Start:New Haven Railroad Station
New Haven, Connecticut·
4.0
(97) review
50 Union Ave, New Haven, CT 06519-1754
9
Start: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.
10
Start:Hollywood Gaming Mahoning Valley Race Course
Youngstown, Ohio·
3.5
(83) review
655 N Canfield Niles Rd, Youngstown, OH 44515-1102
11
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.
12
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
13
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.
14
Start:Quad Cities Symphony Orchestra
Davenport, Iowa·
4.5
(8) review
327 Brady St, Davenport, IA 52801-1508
15
Start: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.
16
Start:German American Heritage Center
Davenport, Iowa·
4.5
(84) review
712 W 2nd St, Davenport, IA 52802-1410
17
Start:Hot Shops Art Center
Omaha, Nebraska·
4.5
(96) review
13th & Nicholas, Omaha, NE 68102
18
Start: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.
19
Start: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.
20
Start:Paladin Brewing
Austintown, Youngstown, Ohio·
4.5
(9) review
6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012
21
Start:Lock 3
Akron, Ohio·
4.5
(98) review
200 S Main St, Akron, OH 44308-1315
22
Start: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
23
Start:Allen County War Memorial Coliseum
Fort Wayne, Indiana·
4.0
(99) review
4000 Parnell Ave, Fort Wayne, IN 46805-1414
24
Start: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.
25
Start:Fun Plex
Omaha, Nebraska·
3.5
(92) review
7003 Q St, Omaha, NE 68117-1649
CHECKLIST
GPS device or app
Download Offline Map
Car charger and portable battery
Water bottles and snacks
Travel pillow and blanket
Sunglasses and sunscreen
First-aid kit
Trash bags
Hand sanitizer and wet wipes
Driver’s license and vehicle registration
Cash and cards
Camera or smartphone
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FAQ
Frequently Asked Questions
What's the driving distance between Boston and Enterprise?
The distance is 2,740 miles
What's the travel time between Boston and Enterprise?
The driving time can vary depending on traffic conditions, but it is typically 48h 59m mins in normal traffic
What are some of the best cities to visit between Boston 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
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A 6-day itinerary in Enterprise
Where else can I travel to if I'm starting my trip in Boston?
We have a lot of great trip options for Boston! See the links below for all the itineraries we created for you