The lore of the great American road trip has been penned into novels, produced on the big screen, and fantasized about by many a traveler. I-90, the northernmost of the east-west interstates, takes you on a three thousand mile journey from Boston to Seattle, or Seatle to Boston depending on where you start.

One of the most iconic aspects of US travel is its interstate system and how easily it connects east to west. The fact that just one road is needed to cross a continent as large as North America opens up so many opportunities for road trips.


The I-90 route is the northernmost route so do plan for this to be a late spring to early fall trip. You will cross mountain ranges and pass through high planes, so plan accordingly and you will have an adventure of a lifetime.

Day 1 - Boston, MA

If you are native to Boston or even Massachusetts, you might roll your eyes at the suggestion to visit Faneuil Hall at Quincy market, and yes it's super touristy but it's fun and a great place for someone not from the area to explore. There are a ton of other spots close by, making it a fun way to begin or end your road trip.

Day 2 - Syracuse, NY

Syracuse is located amidst valleys, lakes, and streams. Lake Onondaga is right next to it with Lake Ontario just 30 miles away. A visit to the great lake may be a little far but alternatives are the Rosamond Gifford Zoo, Erie Canal Museum, and if you time it right you may even encounter The Great New York State Fair!

  • Travel Time - 312 miles, 5 hours and 2 minutes from Boston

Day 3 - Erie, PA

Erie’s primary attraction is Lake Erie itself. Erie is Pennsylvania's only Great Lakes port city and has many coastal beaches and hikes. Presque Isle State Park is a great location to relax and spend some time stretching your legs in nature.

Day 4 - Toledo, OH

Located on the western shore of Lake Erie, Toledo offers another Great Lakes experience. Other options for exploration include the Toledo Museum of Art, Toledo Zoo & Aquarium as well as the Imagination station. The latter is an interactive science center. If you are just looking for something casual the downtown offers riverside walks as well as live music and eateries.

  • Travel Time - 216 miles, 3 hours 32 minutes from Erie

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Day 5 - Chicago, IL

Chicago is a haven for sports, dining, and modern art. You can find a great deal to entertain yourself here depending on your interests. Two recommendations are Millennium Park and Garfield Park Conservatory. Or, perhaps do the most touristy things possible and grab a steak-n-cheese from Monti’s or a deep-dish pizza from Pequod’s Pizza.

  • Travel Time - 245 miles, 4 hours 3 minutes, from Toledo
  • Monti’s - 4757 N Talman Ave Chicago, IL 60625
  • Pequod’s Pizza - 2207 N Clybourn Ave Chicago 60614

Day 6 - La Crosse, WI

La Crosse Wisconson is a small town right on the Mississippi. Aside from exploring and snapping pictures of the northern part of America’s mightiest river you can visit Grandad Bluff and the Shrine of Our Lady of Guadalupe.

  • Travel Time - 282 miles, 4 hours 20 minutes from Chicago

Day 7 - Sioux Falls, SD

Another small town, Sioux Falls is aesthetically located near the falls from which the city is named. You can visit Falls Park to snap some pictures with this lovely natural attraction. Other options to visit are the SculptureWalk & Arc of Dreams Monument and the St. Joseph Cathedral.

  • Travel Time - 299 miles, 4 hours 35 minutes from La Crosse

Day 8 - Wall, SD

No matter which direction you are headed you will begin to see the signs for “Wall-Drug” in the town of Wall, South Dakota. It’s a fun little touristy center where you can spend a few hours exploring, shopping, enjoying one-cent coffees, and taking in the general charm of this little tourist trap in the middle of nowhere.

  • Travel Time - 294 miles, 4 hours 28 minutes from Sioux Falls

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Day 9 - Sheridan, WY

Located in the stunning state of Wyoming Sheridan offers many outdoor adventures at Bighorn National Forest. Other places in Sheridan to enjoy are Crazy Woman Trading Company and King's Saddlery and Museum.

Day 10 - Bozeman, MT

Montana is an absolutely beautiful state with Bozeman being the prize of Big Sky County. Aside from the typical winter sky activities found near Bozeman, Spring brings high waters and rafting on the Gallatin River while Summer is excellent for hiking and outdoor adventure.

Day 11 - Missoula, MT

Nestled into the Rocky Mountains Missoula offers a variety of kayaking, hiking, and biking options with the three major rives and acres of forest surrounding it. If you are looking for something a little more relaxed, consider exploring its historic downtown with its early-century buildings, shops, galleries, dining, and nightlife.

Day 12 - Spokane, WA

Spokane boasts an urban life that is more active than expected this far east in Washington State. Yet, it also has plenty of outdoor activities to enjoy as well. If you are looking for something uniquely delicious try Sante Restaurant & Charcuterie or The Wandering Table where James-Beard-nominated chefs will prepare exquisite meals.

  • Travel Time - 198 miles, 3 hours 20 minutes from Missoula
  • Sante Restaurant & Charcuterie - 404 W Main Ave, Spokane, WA 99201, United States
  • The Wandering Table - 1242 W Summit Pkwy, Spokane, WA 99201, United States

Day 13 - Snoqualmie Pass, WA

Either you’re at the tail end of a long road trip or at the start of one. Regardless, park the car and go for a hike. There are many trails in this area to explore. You won’t regret the exercise with all the driving behind or ahead of you.

Day 14 - Seattle, WA

Celebrate the start or end of this road trip with a visit to Seattle’s waterfront. Pike’s Place Market is a great location to spend a few hours and there are lots of shops and fun restaurants in the area.

  • Travel Time - 54 miles, 52 minutes from Snoqualmie Pass
  • Total Distance - 3,021 miles
  • Total Time - 49 hours and 40 minutes

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