10 Things to See on a Road Trip From Boston to Chicago
Experience the Best of Boston to Chicago on the Open Road
The best things to do on a road trip from Boston to Chicago feature quirky museums filled with dinosaurs or witchcraft and exploring natural marvels like magnificent waterfalls. Though you could power through the 15-hour drive between the 2 cities, why not take your time when there are so many fun things to do along the way?
Experience the open road through the east coast of USA and you’ll create memories to last a lifetime. Find out more about the best things to do on a road trip from Boston to Chicago with this guide.
1. Mary Had a Little Lamb Statue, Sterling, MA
An extremely famous lamb
Good for: Budget, Photo
Head an hour west of Boston to see the Mary Had a Little Lamb Statue, a cute little memorial to the famous lamb with a fleece as white as snow. Mary was a real person, born in Sterling in 1806, and she took the lamb to school one day. A classroom visitor, John Roulstone, is said to have written the beloved poem that children around the world still recite today.
The charming bronze statue commemorates the lamb’s owner, Mary Sawyer, and stands in the Town Common. Sterling is a small town that’s worth a walk around, and there’s a fun-filled agricultural fair every September. Don’t forget to snap a selfie with Mary’s lamb before heading back on the road.
Location: Sterling, MA 01564, USA
Mary Had a Little Lamb Statue, Sterling, MA
2. Underground Railroad Education Center, Albany, NY
Insightful anti-slavery history museum
Good for: History, Families, Couples
A few minutes from downtown Albany, discover the Underground Railroad Education Center, an important American historical museum which explores the horrors of slavery and the work of the Underground Railroad. The Stephen and Harriet Myers Residence was a headquarters for Underground Railroad activity in the Capital Region in the mid-1850s.
Call ahead to schedule your guide and take a 90-minute tour to learn about the Railroad from the perspectives of Stephen Myers, an enslaved man, and Black abolitionists, Stephen and Harriet Myer. If you’ve little ones in tow, there’s a puzzle pack and a colouring book you can download before you visit.
Location: 194 Livingston Ave, Albany, NY 12210, USA
Open: Monday–Friday from 5 pm to 8 pm, Saturday from noon to 4 pm (closed on Sundays)
Phone: +1 518-621-7793
Underground Railroad Education Center, Albany, NY
3. World’s Smallest Church, Oneida, NY
All faiths welcome at this tiny church
Good for: Budget, Photo
Take a short detour from Oneida to see one of the world’s smallest churches, the Cross Island Chapel, in the middle of a pond in central New York state. Built in 1989, this little white church is around 2.8 sq metres inside and just about big enough for 2 people.
There is a small floating jetty next to the church, so you can moor a rowboat. It’s open to all denominations by request and has been the venue for several, very small, weddings. Take a moment to sit and enjoy the peace and the flocks of Canadian geese who make Mason Pond their home.
Location: Oneida, NY 13421, USA
World's Smallest Church, Oneida, NY
4. Niagara Falls, NY
Iconic waterfalls lining the border between Ontario and New York
Good for: Budget, Photo, Adventure
Nothing prepares you for the thunder and spray of the incredible Niagara Falls straddling the Canadian-USA border in New York State. Comprised of 3 waterfalls, at Niagara you can see the American Falls and Bridal Veil Falls, and the Horseshoe Falls on the Canadian side. Join the 8 million visitors who explore Niagara Falls State Park each year, to see one of the Seven Natural Wonders of North America.
Delve deep behind the Falls and discover the Cave of the Winds or embark on an astounding journey to see this natural wonder up close on the Maid of the Mist boat tour. You’ll even receive a souvenir rain poncho.
Location: Niagara Falls, NY 14303, USA
Niagara Falls, NY
5. Eternal Flame Falls, NY
Nature puts on a show
Good for: Budget, Photo
Flames and waterfalls may sound like a Vegas show, but it’s actually a natural phenomenon at the Shale Creek Preserve and Eternal Flame Falls in Western New York State. By itself, Eternal Flame Falls’ modest 9-metre cascades are a pretty sight. However, the natural gas spring in a grotto behind the falls holds an almost eternal flame, giving the site an instant wow factor.
The best time to visit Eternal Flames Falls is in the early springtime when the melt adds power to the falls. Winter has dangerously slippery conditions and is only to be attempted by experienced adventurers. Make sure you wear appropriate shoes.
Location: Eternal Flame Hiking Trail, Orchard Park, NY 14127, USA
Eternal Flame Falls, NY
6. Mazza Vineyards, PA
A prestigious family-owned winery
Good for: Food, Couples
The Mazza family have been making wine at Mazza Vineyards on the shores of Lake Erie since 1972. You can visit their rustic, Mediterranean-style winery year-round to taste the legacy of this Pennsylvania favourite. No reservations are necessary here to enjoy a guided tasting flight through the Mazza portfolio, which includes fortified wines such as port, sherry and even ice wine.
Not a drinker? There’s still plenty to enjoy: try a flight of grape juices including sparkling red grapes, concord grapes and white grapes. On weekends, enjoy mimosa flights with watermelon and pineapple juice. Don’t forget to take home a few bottles as a souvenir.
Location: 11815 E Lake Rd, North East, PA 16428, USA
Open: Monday–Saturday from 9 am to 5.30 pm, Sunday from noon to 4.30 pm
Phone: +1 814-725-8695
Mazza Vineyards, PA
7. Buckland Museum of Witchcraft & Magick, Cleveland, OH
A glimpse into Ohio’s spooky side
Good for: History, Unusual
Taking an anthropological approach to understanding the facts, folklore and superstition that surrounds witchcraft and magic, Buckland Museum of Witchcraft & Magick is around a 10-minute drive south of Cleveland. Book a tour to get the most out of your experience with a guide who is knowledgeable in the pagan arts.
The Buckland collection was inspired by the work and collection of English Wiccan, Gerald Gardener. Check the museum’s website for events listings and visiting exhibits as they often have interesting guest speakers and visiting artist displays. Book your tickets in advance to save a little money.
Location: 2155 Broadview Rd, Cleveland, OH 44109, USA
Open: Thursday from noon to 6 pm, Friday–Saturday from noon to 7 pm, Sunday from noon to 4 pm (closed on Monday–Wednesday)
Phone: +1 718-709-6643
Buckland Museum of Witchcraft & Magick, Cleveland, OH
8. Kelley’s Island, OH
A tiny island with big fun
Good for: Adventure, Food, Unusual
Make a stop 6.4 km north of Marblehead and take the passenger ferry to Kelley’s Island, a diminutive 11.4 sq km island on the western basin of Lake Erie. Kelley’s Island may be small, but it packs a mighty punch when it comes to things to do. Visit the local brewery or 1 of the 2 island wineries, take a bike ride or go kayaking, play putt-putt or visit the museum or art gallery.
You can also see the world’s largest example of the geological phenomenon of glacial grooves here, created by the slow movement of the massive glacier that created the Great Lakes and Lake Erie Islands.
Location: Kelley’s Island, Ohio 43438
Kelley's Island, OH
9. Pokagon State Park, IN
Year-round relaxation and adventure
Good for: Budget, Photo
Take a break from the road and spend a night at Pokagon State Park, a year-round spot for adventure and relaxation near Angola, just off the I-69. In wintertime, you can go cross-country skiing and sledding or ride the on-site toboggan down a 400-metre track at 48 km/h. From spring to autumn, hike and bike ride along the trails, or take a boat, go fishing and enjoy the beaches and swimming lakes.
Book a room at the onsite inn or for something really special, opt for one of the rustic cabins complete with coffee makers and televisions. Alternatively, pitch up a tent or park your RV and spend a night under the stars in this peaceful state park.
Location: 450 Ln 100 Lake James, Angola, IN 46703, USA
Open: Daily from 7 am to 11 pm
Phone: +1 260-833-2012
Pokagon State Park, IN
10. Indiana Dinosaur Museum, South Bend, IN
One of America’s largest dinosaur displays
Good for: History, Adventure
South Bend isn’t just famous as the city that elected Pete Buttigieg as Mayor; it also boasts the Indiana Dinosaur Museum at the intersection of US 31 and US 20. With more than 30 dinosaur skeletons on display, plus more than 40 life-sized dinosaur sculptures, the Indiana Dinosaur Museum offers plenty to enjoy. You’ll get the chance to dig deep in a working excavation site, which uncovered a unique Cretaceous dinosaur called the Edmontosaurus, found with its skin preserved.
Take a guided tour to get the most from your prehistoric experience, and visit the neighbouring Continental Divide Park, where you can snap a selfie more than 250 metres above sea level.
Location: 7102 Lincolnway W Hwy, South Bend, IN 46628, USA
Open: Monday–Friday from 10 am to 5 pm, Saturday–Sunday from 9 am to 5 pm
Phone: +1 574-233-2577
Indiana Dinosaur Museum, South Bend, IN
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