Road trip from Boston to Rockford
All Category
Sights & Landmarks
Food & Drink
Fun & Games
Nightlife
Museums
Shopping
Concerts & Shows
Show more (2+)
All Category
Sights & Landmarks
Food & Drink
Fun & Games
Nightlife
Museums
Shopping
Concerts & Shows
Nature & Parks
Reset
Show less
ITINERARY
20h 19m1,074 miles23 stops
1
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.
2
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.
3
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!
4
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.
5
DCU Center
6
Burnside Fountain
7
Rhode Island School of Design Museum of Art
This innovative and internationally renowned museum showcases more than 80,000 works of art from Paul Revere's silver and caricatures of 18th century Europe, to French Impressionists and the avant-garde works of recent alumni. A 12th-century Japanese Buddha has its own room with benches for meditating.
8
Owl Shop Cigar Lounge
9
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.
10
New Haven Railroad Station
11
Marine Corps League NE Detachment Museum
12
Steamtown National Historic Site
This small museum is all about steam engines and their contribution to America's economy in the 19th century.
13
Basilica of Our Lady of Mount Carmel
14
Hollywood Gaming Mahoning Valley Race Course
15
Paladin Brewing
16
Lock 3
17
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
18
Allen County War Memorial Coliseum
19
Sprucewood Shores Estate Winery
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)
20
Michigan Avenue Bridge
The view from the bridge is one of the best vistas the city has to offer.
21
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
22
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.
23
Anderson Japanese Gardens
Anderson Japanese Gardens is proud of its longstanding reputation as one of the highest quality Japanese gardens in North America. Our passion, however, is how the Garden positively impacts individuals and the communities where they live. We are committed to presenting first-class programs, events, and opportunities that bring people together in this uplifting natural setting.
Customize this Trip
OVERVIEW
1
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.
2
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.
3
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!
4
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.
5
Start:DCU Center
Worcester, Massachusetts·
3.5
(93) review
50 Foster Street, Worcester, MA 01608-1305
6
Start:Burnside Fountain
Worcester, Massachusetts·
3.5
(8) review
Main St Behind City Hall, Worcester, MA 01608-1821
7
Start:Rhode Island School of Design Museum of Art
Providence, Rhode Island·
4.5
(981) review
This innovative and internationally renowned museum showcases more than 80,000 works of art from Paul Revere's silver and caricatures of 18th century Europe, to French Impressionists and the avant-garde works of recent alumni. A 12th-century Japanese Buddha has its own room with benches for meditating.
8
Start:Owl Shop Cigar Lounge
New Haven, Connecticut·
4.5
(9) review
268 College St, New Haven, CT 06510-2404
9
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.
10
Start:New Haven Railroad Station
New Haven, Connecticut·
4.0
(97) review
50 Union Ave, New Haven, CT 06519-1754
11
Start:Marine Corps League NE Detachment Museum
Scranton, Pennsylvania·
5.0
(8) review
1340 Alder Street, Scranton, PA
12
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.
13
Start:Basilica of Our Lady of Mount Carmel
Youngstown, Ohio·
4.5
(7) review
343 Via Mount Carmel Ave, Youngstown, OH 44505-3037
14
Start:Hollywood Gaming Mahoning Valley Race Course
Youngstown, Ohio·
3.5
(83) review
655 N Canfield Niles Rd, Youngstown, OH 44515-1102
15
Start:Paladin Brewing
Austintown, Youngstown, Ohio·
4.5
(9) review
6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012
16
Start:Lock 3
Akron, Ohio·
4.5
(98) review
200 S Main St, Akron, OH 44308-1315
17
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
18
Start:Allen County War Memorial Coliseum
Fort Wayne, Indiana·
4.0
(99) review
4000 Parnell Ave, Fort Wayne, IN 46805-1414
19
Start: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)
20
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.
21
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
22
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.
23
Start:Anderson Japanese Gardens
Rockford, Illinois·
4.5
(863) review
Anderson Japanese Gardens is proud of its longstanding reputation as one of the highest quality Japanese gardens in North America. Our passion, however, is how the Garden positively impacts individuals and the communities where they live. We are committed to presenting first-class programs, events, and opportunities that bring people together in this uplifting natural setting.
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
Unlock Effortless Travel Planning
Create your dream trip in minutes by this prompt. Try now!
EXPLORE MORE
Discover Exciting Road Trip Inspirations
Boston to Denver
1,981 miles
36h 1m
30 stops
Food & DrinkSpas & WellnessOtherShoppingFun & Games
Boston to Detroit
720 miles
14h 11m
28 stops
Food & DrinkSights & LandmarksToursMuseumsNature & Parks
Boston to San Francisco
3,113 miles
55h 13m
42 stops
Sights & LandmarksNature & ParksWater & Amusement ParksMuseumsFun & Games
Boston to Phoenix
2,672 miles
48h 7m
41 stops
MuseumsOutdoor ActivitiesFun & GamesFood & DrinkSpas & Wellness
Boston to Seattle
3,044 miles
54h 37m
34 stops
Sights & LandmarksFood & DrinkFun & GamesMuseumsShopping
Boston to Brooklyn
216 miles
4h 45m
23 stops
Fun & GamesToursConcerts & ShowsNightlifeSights & Landmarks
EXPLORE OTHER
Check Out Different Road Trip Options
Reno to Gilbert
770 miles
15h 12m
14 stops
MuseumsOutdoor ActivitiesSights & LandmarksConcerts & ShowsTours
Oakland to Lorain
2,435 miles
42h 21m
32 stops
Sights & LandmarksNature & ParksWater & Amusement ParksMuseumsFun & Games
Reno to Sunrise Manor
457 miles
8h 54m
7 stops
Sights & LandmarksConcerts & ShowsMuseumsOutdoor ActivitiesNightlife
New Orleans to Spring Valley
1,735 miles
30h 46m
39 stops
Nature & ParksMuseumsConcerts & ShowsSights & LandmarksFood & Drink
Mesa to Port Arthur
1,215 miles
21h 39m
27 stops
Spas & WellnessNightlifeFun & GamesMuseumsTraveler Resources
Bridgeport to Oyster Bay
69 miles
1h 39m
19 stops
Concerts & ShowsBoat Tours & Water SportsFun & GamesShoppingTours
FAQ
Frequently Asked Questions
What's the driving distance between Boston and Rockford?
The distance is 1,074 miles
What's the travel time between Boston and Rockford?
The driving time can vary depending on traffic conditions, but it is typically 20h 19m mins in normal traffic
What are some of the best cities to visit between Boston and Rockford?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Rockford?
There are plenty! Here are some stops you shouldn’t miss on your way to Rockford
What’s the weather like in Rockford?
The weather in Rockford is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Rockford in January
Weather in Rockford in February
Weather in Rockford in March
Weather in Rockford in April
Weather in Rockford in May
Weather in Rockford in June
Weather in Rockford in July
Weather in Rockford in August
Weather in Rockford in September
Weather in Rockford in October
Weather in Rockford in November
Weather in Rockford in December
Interested in a detailed plan for your time in Rockford?
Plan your dream Rockford trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Rockford
A 2-day itinerary in Rockford
A 3-day itinerary in Rockford
A 4-day itinerary in Rockford
A 5-day itinerary in Rockford
A 6-day itinerary in Rockford
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