With the holidays quickly approaching and the weather beginning to turn winter is almost here. As the days grow darker and colder, it’s easy to just cozy up indoors, but for those in search of adventure, this season offers an opportunity to explore cozy getaways and charming small towns. Whether you like a little sports action cozying up in a cabin with a hot drink, or discovering winter festivals, the Midwest has something special to offer. From the rolling hills of Wisconsin to the bustling streets of Chicago lit up with holiday cheer, these winter weekend escapes promise both relaxation and adventure. Here are some of the best spots to visit in the Midwest this winter.
Chicago, Illinois
Bustling City: 3-hour drive from Indianapolis
Chicago combines the bustle of the city and a mix of festive cheer, vibrant culture, and plenty of outdoor fun. The Windy City offers a variety of winter activities that cater to every type of adventurer. From skating at iconic ice rinks to wandering through lit-up winter wonderlands to enjoying cozy indoor experiences, here’s how to make the most of a day exploring winter activities in Chicago.
Visit Christkindlmarket: No winter day is complete without a visit to the Christkindlmarket in Daley Plaza. This European-style Christmas market offers festive stalls selling unique holiday gifts, artisan crafts, and seasonal treats similar to the one in Carmel. Warm up with a cup of Glühwein or a mug of hot cocoa, and get your holiday shopping done with some unique finds.
Grab dinner at Cabra: If you’re looking for a great place to take your girl gang for dinner, Cabra is a must-try. Their menu is tapas style, so it’s perfect for ordering a bit of everything to share. They have great drinks and beautiful city views that you won’t want to miss.
Ice Skating at the Willis Tower Skydeck: If you’re craving one more dose of winter magic, head to the Willis Tower Skydeck. During the winter, the Skydeck offers ice skating on top of one of Chicago’s tallest buildings. There’s no better way for you and your girls to take in the breathtaking panoramic views of the city.
Walk through the lights at the Botanical Garden: If you’re in the city between November 15 and January 5, make sure to end your evening under the lights as you stroll through the grounds of the Botanical Garden for Lightscape. It’s similar to Winterlights at Newfields, but the grounds of the garden are extensive, and you’ll definitely walk off your dinner. Grab a cup of hot cocoa and enjoy the Christmas carols as you get into the holiday spirit.
Madison, Wisconsin
Outdoor Adventure: 5-hours from Indianapolis
Madison is a vibrant college town that transforms into a winter wonderland filled with cozy spots, snowy landscapes, and tons of outdoor activities. Whether you’re an outdoor adventurer, a foodie, or someone who loves to explore arts and culture, the city has a variety of activities to make your winter day unforgettable.
Ice Skating at Tenney Park: For girls who love to get outside and explore, Tenney Park is one of the best spots for ice skating. The park features a scenic lagoon with an outdoor rink, and you can rent skates on-site. Skating here offers views of the surrounding trees and the lake, creating a peaceful, serene winter experience. If you’re feeling adventurous, you can also try cross-country skiing or snowshoeing on the park’s nearby trails.
See the Lights on State Street: Enjoy the winter evening with a leisurely walk along State Street, Madison’s main walking path. During the winter months, the street is beautifully lined with holiday lights, and the festive atmosphere is magical. Check out unique boutiques, stop by one of the city’s many cozy coffee shops, or just enjoy the seasonal displays and the twinkling lights above you.
Warm Up with a Nightcap at The Old Fashioned: Finish your winter day with a nightcap at The Old Fashioned, a Madison bar known for its classic cocktails and hearty comfort food. The warm, rustic atmosphere is the perfect way to end a winter evening in Madison.
Traverse City, Michigan
Foodie & Festival Haven: 6-hour drive from Indianapolis
Skiing & Snowboarding at Crystal Mountain: For the girl who loves hitting the slopes, Crystal Mountain is just a short 45-minute drive from Traverse City. This family-owned resort offers top-notch skiing and snowboarding for all skill levels. In addition to skiing, you can try snowshoeing, snow tubing, and even winter zip-lining.
Wine Tasting at Winter Vineyards: Traverse City is famous for its wineries, and many of them stay open year-round. Cozy up by the fire while you sip a glass of wine with fewer crowds.
Winter Festivals: Ring in the New Year the Traverse City Way – with a 600 lb. cherry dropping on Front St. The CherryT Ball Drop happens on December 31st. Enjoy the giant glowing cherry lit up with fireworks.
No matter what type of winter escape you’re seeking, the Midwest has something to offer. Whether you’re drawn to the hustle and bustle of Chicago, the lakeside charm of Madison, or the snowy adventure of Traverse City’s ski slopes and vineyards, these destinations will leave you with an unforgettable winter weekend. Bundle up and get ready to make lasting memories on your next winter adventure in the heart of the Midwest!
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