DETOUR DUJOUR: The Ultimate Road Trip Guide to I-90, Boston to Seattle (2023)

Altes Sturbridge Dorf

Sturbridge, MA

If you start in Boston, there are tons of places to visit, from the New England Aquarium to Faneuil Hall (where you can choose from dozens of different food stands for a taste of Boston) to the Freedom Trail and the Museum of Science. As far as Boston hotels go, the Liberty Hotel is a former prison with countless subtle nods to the building's past.

From Boston, stop at Old Sturbridge Village in Sturbridge, MA, where you can literally be transported back in time to the 1830s. What sets this open-air living history museum apart is that it happens to be the largest living history museum northeast. Here you can experience what life was like in the late 1700's to mid 1800's. There are over 40 original buildings and the staff is always dressed with a focus on 100% authenticity. The best time to visit to avoid crowds is spring and fall. In fact, fall is the perfect time to visit and take beautiful photos, as the town is covered in stunning fall foliage. BONUS: If you are visiting during Thanksgiving, they have an out of this world buffet.


Six Flags New England

Six Flags New England is quite a notable amusement park as it actually dates back to 1870 and has a reputation as the oldest Six Flags Park. The park is spread over 235 hectares and if you buy a park pass you can also go to the water park. If you go, be sure to ride the Thunderbolt, a wooden roller coaster that has been in operation since 1941. It's not exactly a quick stop off the highway, but it's an incredibly fun way to spend the day!


The smallest church in the world.

The next stop on I-90 is "The World's Smallest Church." Perched on a small wooden platform on Sconondoa Road in Oneida, the non-denominational Cross Island Chapel is absolutely beautiful. The 3-foot by 6-foot church was built in 1989 and now stands on a small dock right in the middle of the pond. It is available for meditation and special occasions.


Jell-O Gallery Museum

From "The World's Smallest Church" to the Jell-O Gallery Museum in Le Roy, NY! Even if you're not a fan of jelly, every road trip needs a weird and offbeat museum detour. Here, for just $4.50 admission, you can learn everything you ever (or never) wanted to know about gelatin. Then, while you're in Le Roy, dine at Smokin' Eagle for delicious barbecue before heading back on the highway.


Eternal flame


Orchard Park, New York

Then drive to Orchard Park, New York to see Eternal Flame Falls. This is a phenomenal natural wonder and well worth the detour from I-90 to visit. Park on Chestnut Ridge Road and prepare for a short 15 minute walk to the falls. You will smell a rotten egg smell (a result of the natural gas causing the fire) as you approach the tiered falls, which drop about 30 feet. Here you will notice a small grotto, within which is a flame approximately 4 to 8 inches high, ignited by natural gas escaping from the spring. It really is an amazing natural wonder.


Willoughby Ghost Walk

If you're taking the interstate through Willoughby, why not take a walk on the spooky side? Willoughby Ghost Walk Tours run from June to October and offer guided walking tours of downtown Willoughby. You'll learn all about the town's haunted history, including the legends of strange phenomena that have been reported over the years. The tour covers 12 blocks and takes just under two hours.


Superman's birthplace

If you're a fan of Superman (especially the comics), make a pilgrimage to the home of Jerry Siegal, the creator of Superman. Outside the house you can see a sign and the iconic Superman logo commemorating the previous owner of the house. Jerry Siegel and Joe Shuster came up with the idea of ​​a superpowered hero in 1933. Both boys lived on the same street and came from Jewish immigrant families. The current owners of the house where Superman was "born" are very friendly to people on Superman pilgrimages, and Superman memorabilia is scattered throughout the property.


A house and museum of Christmas stories

Cleveland, OH

If you are a fan of the movie "A Christmas Story", you should definitely stop by the house where the movie was filmed... even if it is in the height of summer! It is located on West 11th Street in Cleveland and tours are available. They even encourage you to touch the exhibits and even recreate your favorite scenes for photos. The tour can take about an hour, so if you have the time, it's almost as good as being in the movie.

When staying in Cleveland, there are some great hotel options. The Glidden House is an amazing 1910 mansion converted into a B&B, and the Hyatt Regency at The Arcade offers a great location. For a meal try Lucky's Cafe or Melt.


Olde Avon Dorf

If you enjoyed Sturbridge Village in Massachusetts, take a detour off I-90 to Olde Avon Village in Avon, Ohio. Here you can step back in time and see what life was like in the mid-19th century. There are shops, houses and pretty much everything you could want in an authentic 19th century village. Then head back to the 21st century and get back on the road!


pokagon state park

When you're ready to stretch your legs again, stop by Pokagon State Park near Angola, Indiana. The park's name comes from Leopold and Simon Pokagon, the last two chiefs of the Potawatomi tribe. If you're looking to stay in Indiana, you should check into the Potawatomi Inn, a fairly popular tourist accommodation in the Midwest. Throughout the park you will find beautiful stone and log buildings, wide open fields and meadows, rolling hills and even wetlands.




Michigan City, IN

Take a detour off I-90 to Washington Park Beach in Michigan City, IN and visit the Michigan City Lighthouse or stroll along the boardwalk. There's also a two-acre zoo right across from the beach and playgrounds for the little ones. The park is open from 6 am to 10 pm and costs $2 on weekdays and $5 on weekends. There is also plenty of parking!


michael jackson house

If you're a fan of Michael Jackson, you definitely want a photo at his childhood home in Gary, Indiana, which is right off the highway. The best time to visit is in August, when there is usually a Michael Jackson themed event.


the second city

If you love Saturday Night Live or just like improv comedy, then you need to visit the improv mecca: The Second City in Chicago. This is where the best SNL performers got their start.

TIP: When you buy tickets through the Second City website, you can usually get a great deal at a nearby restaurant at the same time. Chicago Dinner and Show: The Perfect Night on the Town!

And when you're looking for a hotel in Chicago, the options are nearly endless. Hotel Lincoln, Hotel Monaco, Hotel Burnham... take your pick! You all are great.


Legoland Discovery Center

On your way out of Chicago, visit the Legoland Discovery Center in Schaumurg, IL. There are over 3 million Lego bricks here and you can spend the day exploring with kids. Remember that Legoland is a children's attraction and all adults must be accompanied by a child. However, if you have a child around, this is a must!


Goebbert's Pumpkin Patch

If you're visiting in the summer and fall, be sure to check out Goebbert's Pumpkin Patch in Pingree Grove. There is so much to do, especially in the fall, from a pumpkin-eating dinosaur to a hay bale maze and any other outdoor activity you can think of. Oh, and the puppets are absolutely adorable.

TIP: Go on a weekday to avoid the fall weekend crowds. And don't forget to stop by the cafeteria and gift shop!


Kegonsa Lake State Park

I-90 then heads to Wisconsin! Lake Kegonsa State Park is considered "one of southern Wisconsin's best kept secrets." This state park features a 3,200-acre lake, woods, beach for swimming, fishing, boat launch, and camping. There are countless hiking trails and picnic spots if you just want to get some fresh air and soak up the sun!


pink elephant

Next up: Extravagant roadside photo shoot! A giant pink elephant with glasses is standing at a gas station. His name is "Pinkie" and he was installed at the gas station in the late 70s, today he is a Citgo. It is definitely the most adorable gas station on I-90!


Circus World Museum

If you're still in the mood for a slightly more original adventure, visit the Circus World Museum in Baraboo, Wisconsin. The Ringling Bros. Circus was founded in this city in 1884 by five brothers. In fact, they called the town the "winter quarters" of the Ringlingville circus. Between 1897 and 1918, several buildings were erected along the Baraboo River in what is now the "largest surviving group of original circus buildings" in the United States. Here you can see souvenirs and learn all about the history of the circus, which is actually quite interesting.

And if you want to read a good book along the way, Katherine Dunn's 'Geek Love' will definitely put you in the mood to enjoy your time at Circus World Museum to the fullest.


witches cannon

Wisconsin Dells, WI

From clowns to witches... in Wisconsin Dells, skip the water parks (did you know Wisconsin Dells has more waterslides per capita than anywhere else in the world?) and head to Witches Gulch. It's like something out of Lord of the Rings! Admission is only $5 and it is an absolutely stunning geological wonder. The Gulch is a slotted canyon surrounded by lush forest. Pet friendly and definitely worth a visit if you're in the area.

and when youAgainWe can't wait to get in on the water park action in the water park capital of the world, we love the wacky deals at the Kalahari Resort!


Mill Bluff State Park


Camp Douglas, WI

If you're still in the mood for some outdoor fun, your next stop off the highway is Mill Bluff State Park near Camp Douglas, Wisconsin. This state park has beautiful towering cliffs, swimming areas, a campground, and plenty of places to hike or relax after a long day of driving.

Depending on the time of year you choose to travel I-90, it's important to note that the weather can affect your trip. Snow and strong winds will harass you from Minnesota to Montana, especially in winter. The snowplows do a good job, but if there's a storm you could get stuck, so be prepared before you embark on this journey. Also, keep in mind that between Rapid City and the Black Hills you are at an exceptionally high elevation, which means it's a bit cooler in that area. Depending on the time of year, pack accordingly. In fact, you can expect freezing temperatures in South Dakota, Wyoming, and Montana in the dead of winter. Think antifreeze, winter tires and don't run out of gas.


How do you plan the ultimate road trip? ›

10 Tips for Planning a Fantastic Road Trip
  1. Start planning sooner rather than later. ...
  2. Take advantage of planning tools. ...
  3. Prep your car. ...
  4. Pack a roadside emergency kit. ...
  5. Add side trips to your itinerary. ...
  6. Consider an epic road trip that's all about the route. ...
  7. Be realistic about your total mileage.
Apr 1, 2022

Is there a website to plan a road trip? ›

An increasingly popular app (and website) for mapping and planning a road trip is the aptly named Roadtrippers. Utilizing this tool, users can create road trip maps similar to those found in google maps.

How long does the ultimate road trip take? ›

The Perfect Road Trip Map

The road trip accounts for 224 hours driving, or 9.33 days, that treks over 13,000 miles (13,699 to be exact). Olson suggests that you take two to three months to complete the epic journey across the continental United States.

How do you know if your car can make a long trip? ›

How to get your car ready for a road trip
  1. quality auto coverage starts here. When you drive with quality coverage, you drive with peace of mind. ...
  2. Check your car's battery. ...
  3. Inspect belts and hoses. ...
  4. Top off fluids and replace filters. ...
  5. Verify lights and electrical equipment are working. ...
  6. Check the brakes. ...
  7. Inspect tires.

How often should you stop on a road trip? ›

Take frequent breaks. Never think that you must make a long drive in one stretch. Take a break approximately every two hours. If you are driving on an interstate highway, state sponsored rest areas will provide you with a great place to stretch your legs, grab a snack, and use the restroom.

Are Triptiks free? ›

The AAA Triptik Travel Planner is a route planner of the American Automobile Association. Triptik offers ready-to-use maps in the US and CANADA. This route planner and maps are available for free on

How many miles a day can you drive on a road trip? ›

As a general rule, it's safe to drive for no longer than eight hours a day, taking breaks of at least 15 minutes every two hours. This means you can safely drive for around 500 miles, not taking into account external factors such as slowing for tolls, traffic, travelling with children, and tiredness.

Can you take a high mileage car on a trip? ›

An older or high-mileage vehicle that is regularly maintained should be safe to drive on a road trip.

How many miles a day should I road trip? ›

For every 4.5 hours driving you should take breaks amounting to 45 minutes. For long-distance driving, this means you can drive around 500 miles safely in a day. You should adjust this figure based on the speed limit and likelihood of other circumstances such as toll roads, fatigue, and extended traffic or breaks.

Is there an app to plan a road trip with multiple stops? ›

RouteXL is a go-to route planner for multiple delivery destinations. It helps individuals and businesses find the best multi-stop routes for pickup, delivery, and services. The free version of RouteXL allows up to 20 stops per route while the month per user or paid options allow up to 100 and 200 addresses per route.

Is there an app to plan a road trip? ›

Roadtrippers is the #1 road trip planning tool in the USA and Canada, with more than 38 million trips planned to date covering more than 42 billion miles. Plan your road trip with friends or find an amazing place nearby you never knew existed.

How do I make my road trip less boring? ›

Road Trip Boredom Busters
  1. Find the Alphabet. Spot each letter of the alphabet, in order, on any form of text outside the car. ...
  2. Play Window Bingo. Print blank bingo cards before you leave. ...
  3. Play a Geography Name Game. Say the place name of any city, state, country, or continent in the world.
May 20, 2022

When should I stop taking my car on long trips? ›

As a general rule, it's best to take a break of at least 15 minutes every two hours, and to not drive for more than eight hours in a day, to ensure you stay alert and avoid the associated risks of driving for too long without a rest.

How do you prepare a high mileage car for a long road trip? ›

Two to Four Weeks Before You Go
  1. Get any major repairs done. ...
  2. Check the coolant. ...
  3. Check the tires. ...
  4. Check the spare tire. ...
  5. Check the glovebox. ...
  6. Get any scheduled maintenance done. ...
  7. Check the tires again. ...
  8. Clean out your car.
Mar 4, 2019

Should I service my car before long drive? ›

If a service is due, do it before the trip. If service is not due, just do a check-up before leaving. But do a wheel alignment both before the trip (if not recently done) as well as after coming back. If its an emergency,then go ahead with a routine check from local mechanic and move on.

When should you stop gas on a road trip? ›

You can use your car's range to figure out approximately where and when you should stop for gas. There are times when you may be on a stretch of road with no rest stops for 60 miles or more, so leave a little bit of a buffer for your car's range.

What should I eat before a long drive? ›

Here are our top picks for healthy road trip snacks.
  • Beef jerky. This road trip snack is packed full of protein, which is one of the best ways to satisfy your hunger. ...
  • Popcorn. ...
  • Hard-boiled eggs. ...
  • Protein bars. ...
  • String cheese. ...
  • Carrots. ...
  • Grapes. ...
  • Hummus and celery.

How often should you get gas on a road trip? ›

How often should you stop for gas on a road trip? You should stop for gas on a road trip every three hours to refuel and stretch your legs. It's a good idea to plan your route to incorporate these stops, as well as mapping out where the cheapest gas stations are.

Does Google Maps have a road trip planner? ›

Google Maps has a route planning capability. You can even plan a route for many locations using Google Maps. It can serve a variety of purposes aside from driving, such as walking and biking.

How do I prepare for a 1000 mile road trip? ›

5 Essentials to Prepare Your Car for a 1,000+ Mile Road Trip
  1. Check your coolant.
  2. Maintain your tires.
  3. Clean out your car.
  4. Check your air filter.
  5. Check your suspension and alignment.

How many miles should you drive a day on a road trip? ›

For every 4.5 hours driving you should take breaks amounting to 45 minutes. For long-distance driving, this means you can drive around 500 miles safely in a day. You should adjust this figure based on the speed limit and likelihood of other circumstances such as toll roads, fatigue, and extended traffic or breaks.


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