Chicago To Worcester: The Underrated Road Trip

In this time of uncertainty, the only certainty is that you’re safer not using public transportation. Southern Illinois residents love to take the drive up to Chicago for a weekend getaway, but what if we want to extend the vacation? We believe that Boston is the best place to go for those looking for a fun road trip. We’ll provide you with basic details about where to go and the most interesting landmarks along the way. You’ve already been to Chicago, so we won’t tell you what to do there!

If you’ve never been to Niagara Falls, we recommend spending part of your first day there. The Canadian side of the park is much more scenic, but you might have trouble getting in while COVID is resurging. From there, we recommend one of two routes. The first involves driving up along the Great Lakes, taking pit stops as necessary. The second involves going down to the Finger Lakes, where you’ll find many camping and hiking opportunities. Check out the Finger Lakes Trail, which goes all the way around the lakes.

If you chose to go the Great Lakes Route, find a Fajita Grill for a lunch option we don’t have in Illinois. From there, you will head along I-90 toward Albany. Should you wish to stop there, you might try finding a show at the Egg. Yeah. There’s a landmark called the Egg. If you chose to go the Finger Lakes route, we suggest a detour through NYC. Walk around Manhattan. Take a trip along the High Line, an elevated park. Central Park is another fun option if you’ve never been there. 

From here, you have another option. If you chose the northern route, then you might take a long detour up into New Hampshire for some strenuous hiking or sightseeing in the White Mountains. You’ll find some of the most glorious views East of the Mississippi. If you chose the southern route, you’ll probably want to start driving straight toward Boston.

About an hour away from Boston is the fun, historic town of Worcester. This is a great pitstop if you’re just looking to stretch your legs. Another option is to spend the night here if you would otherwise find yourself in Boston late at night. Trust us: you don’t want to experience Boston traffic before it’s absolutely necessary! When you arrive, check out the Mechanics Hall, the American Antiquarian Society building, or take a drive up Skyline to the Massachusetts Vietnam Veterans Memorial.

Once in Boston, we have one big piece of advice: take it all in. This city is one that preserves its history extraordinarily well. You can feel the colonial vibe just walking down the streets

We recommend hitting a brewery to take the edge off your drive, or go whale watching depending on the season. Once you’re feeling settled into your hotel, check out the Waterfront or the Freedom Trail. Catch a game at Fenway Park. Boston Common is the most beautiful park in the city, and you shouldn’t leave until you’ve taken a stroll there. Last but not least, find the Bodega! It’s hidden well.

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