The Best Things to Do on a Road Trip from Chicago, Illinois to Windsor, Vermont

A road trip from Chicago, Illinois to Windsor, Vermont is a journey full of beautiful sights and exciting adventures. This cross-country route spans over 1,000 miles and passes through some of the most beautiful scenery in the United States. One of the highlights of this trip is the halfway point, Westfield, NY. This peaceful town offers plenty of great food, charming boutiques and a fitting rest stop on your journey. With this in mind, here are the top five things to do on your trip with a one paragraph description of why they should visit.

Exploring the Dunes at Sleeping Bear Dunes National Lakeshore

The Sleeping Bear Dunes National Lakeshore is a 35-mile stretch of pristine shoreline which features lush forests, vast dunes, and crystal clear waters. This is a must-visit spot for anyone who loves hiking, swimming, or just lounging on the beach. The natural beauty here is breathtaking and must be seen to be believed. For a unique viewpoint, take in the panoramic views of Lake Michigan and the surrounding sand dunes from the top of the 400-foot high Dune Climb. Fun fact: the dunes were named "Sleeping Bear" after Native American legend which tells the story of a mother bear and her two cubs who swam for miles to reach the shore of Lake Michigan, where they slept and eventually turned into sand dunes.

Touring the City of Milwaukee

Milwaukee, Wisconsin sits on the shores of Lake Michigan and boasts excellent dining and entertainment options. One can visit one of the many breweries and distilleries or the Harley Davidson Museum. The city’s downtown area offers picturesque views and art that is sure to please. Visit attractions like the Milwaukee Art Museum or the Milwaukee Riverwalk. Fun fact: The original “Bronze Fonz” statue commemorating the popular TV icon Arthur Fonzarelli from “Happy Days” sits on the Milwaukee Riverwalk.

Experiencing the Beauty of Niagara Falls

No road trip from Chicago to Windsor would be complete without a stop at Niagara Falls. This natural wonder of the world is a true marvel of nature. Visitors can experience the beautiful views of the cascading water or go on a boat tour for an up-close and wet experience. The falls are surrounded by well-groomed gardens, a boardwalk and observation decks. Fun fact: Niagara Falls is composed of three waterfalls: Horseshoe Falls, American Falls and Bridal Veil Falls.

Discovering the Rich History of Bennington, Vermont

Bennington, Vermont is steeped in history and natural beauty, and this makes it an ideal location for a stopover on your road trip. Start with a visit to the Bennington Battle Monument, which was built to commemorate the Battle of Bennington in 1777, a pivotal moment in the American Revolution. Also in the city is the Bennington Museum with the largest collection of Grandma Moses artwork, a Vermont artist known for her folk art and paintings of the rural countryside. Fun fact: Bennington, Vermont is home to the oldest continuously operating corn maze in North America, which has been attracting visitors for over 20 years.

Unwinding in the Charm of Historic Woodstock, Vermont

Wrapping up this journey through a charming little town like Woodstock is a perfect way to end your road trip. The town is known for its preservation of the historic old buildings that house various unique shops, eateries and hotels. Make time to explore the Woodstock Village Green and the nearby Marsh-Billings-Rockefeller National Historical Park. Enjoy a special meal at one of the farm-to-table restaurants, or grab a scoop of locally-produced ice cream to end the day on a sweet note. Fun fact: The Marsh-Billings-Rockefeller National Historical Park has been called “The Birthplace of American Forestry,” historically significant for the conservation of natural resources and the sustainability of American forests.

In conclusion, this is a journey that takes approximately 16 hours of driving time excluding all stops, but given the multiple fascinating stops, it is highly recommend for the road trip enthusiast. Anyone looking for a change of scenery, a combination of natural wonder, and cultural history should take a moment and enjoy the drive.