10 Year-Round Things to Do in Highland Park, Illinois That You’ll Love

Key Takeaways Highland Park, Illinois, offers a variety of year-round activities, from outdoor adventures to cultural attractions that cater to all ages and interests. Whether you’re exploring

10 Year-Round Things to Do in Highland Park, Illinois That You’ll Love

Key Takeaways

  • Highland Park, Illinois, offers a variety of year-round activities, from outdoor adventures to cultural attractions that cater to all ages and interests.
  • Whether you’re exploring the local parks, enjoying live music, or visiting the town’s historic sites, Highland Park offers a perfect mix of nature and culture.
  • The charming suburb of Highland Park combines outdoor activities, educational experiences, and vibrant community events, making it an ideal destination for families, nature lovers, and culture enthusiasts.

Table of Contents

  1. Visit the Chicago Botanic Garden
  2. Stroll Through Downtown Highland Park
  3. Explore the Ravinia Festival
  4. Hike at the Skokie Lagoons
  5. Discover the Highland Park History Museum
  6. Relax at Rosewood Beach
  7. Take a Bike Ride on the Green Bay Trail
  8. Attend a Concert at Ravinia Pavilion
  9. Visit the Molly’s Cupcakes Shop
  10. Explore the Sunset Woods Park

Located just north of Chicago, Highland Park, Illinois, is a charming suburban town known for its rich cultural heritage, natural beauty, and vibrant community. The city is home to a mix of historic landmarks, stunning parks, and unique attractions, making it a perfect destination for those looking for a blend of outdoor activities, culture, and relaxation. With the Chicago Botanic Garden, world-class concerts at Ravinia, and numerous trails and parks to explore, Highland Park offers year-round activities for residents and visitors alike. Whether you’re strolling through its scenic parks or taking in live music at a historic venue, there’s always something to do in this picturesque town.

1. Visit the Chicago Botanic Garden

One of the crown jewels of Highland Park is the Chicago Botanic Garden, a stunning 385-acre garden featuring a vast array of themed gardens, walking paths, and water features. Whether you visit in spring to witness the blooms or during the fall when the gardens are ablaze with vibrant colors, the Chicago Botanic Garden offers a picturesque and tranquil experience year-round. With 27 gardens to explore, from the Japanese Garden to the Rose Garden, there’s something for every visitor to enjoy.

The garden also offers educational programs, guided tours, and seasonal events, making it an excellent destination for families, gardening enthusiasts, and nature lovers. The Chicago Botanic Garden is not only a place to relax and enjoy nature but also a place to learn and grow, offering a variety of workshops and community programs. It’s a must-see for anyone visiting Highland Park.

2. Stroll Through Downtown Highland Park

Highland Park’s downtown area is a charming and vibrant spot filled with shops, restaurants, and cafes. Perfect for a leisurely stroll, the downtown area provides a great way to experience the town’s lively atmosphere and beautiful surroundings. Whether you’re window shopping, enjoying a delicious meal, or stopping for a coffee at one of the local cafes, there’s always something to discover in this bustling area.

In addition to its many shops and eateries, downtown Highland Park hosts several events throughout the year, including farmers’ markets, festivals, and street fairs. It’s a great place to experience the local culture, meet the community, and support small businesses. Whether you’re visiting for a day or planning a longer stay, the heart of Highland Park offers something for everyone.

3. Explore the Ravinia Festival

The Ravinia Festival is one of the most iconic cultural venues in the region, offering a range of performances, including classical music, jazz, and contemporary artists. Located just outside of downtown Highland Park, Ravinia provides an unparalleled music experience, with both indoor and outdoor concert spaces. The festival’s outdoor lawn area is perfect for a summer evening concert under the stars, and there are plenty of dining options for a full night out.

Ravinia is not only known for its summer festival but also for its year-round programming. The venue hosts performances throughout the year, so whether it’s a summer evening concert or a winter symphony performance, there’s always a reason to visit. It’s an ideal place to experience world-class music in a relaxed, open-air environment.

4. Hike at the Skokie Lagoons

For outdoor enthusiasts, the Skokie Lagoons offer a beautiful natural setting for hiking, birdwatching, and nature walks. The lagoons themselves are a series of man-made wetlands, making it a serene spot to enjoy wildlife and picturesque views. With over 3 miles of trails to explore, the area is perfect for hiking, cycling, and even cross-country skiing in the winter months.

The Skokie Lagoons are also home to a variety of wildlife, including birds, fish, and small mammals, making it an excellent spot for nature lovers to observe and learn about local species. Whether you’re out for a peaceful walk or a more adventurous hike, the Skokie Lagoons offer a year-round outdoor retreat just a short distance from Highland Park.

5. Discover the Highland Park History Museum

The Highland Park History Museum is a great way to learn more about the history of this charming town. Located in a historic building, the museum offers exhibits showcasing Highland Park’s past, from its founding to its growth into the vibrant community it is today. The museum’s interactive displays and artifacts provide a hands-on experience, making it perfect for history buffs and visitors who want to delve deeper into the town’s heritage.

The museum also offers educational programs, workshops, and guided tours that are perfect for individuals and families alike. It’s a wonderful way to learn more about Highland Park while also gaining insight into the broader history of the region. Whether you’re interested in local history or simply want to explore a unique part of the town, the Highland Park History Museum is an excellent destination.

6. Relax at Rosewood Beach

Rosewood Beach is one of Highland Park’s most popular outdoor destinations, offering visitors a scenic, peaceful escape along the shore of Lake Michigan. The beach features a beautiful stretch of sand where visitors can relax, swim, or simply enjoy the view of the water. It’s a great place to bring a picnic, soak up the sun, or take a quiet walk along the shoreline. Whether you’re looking to cool off on a warm summer day or enjoy the calming atmosphere in the winter months, Rosewood Beach is a local favorite for year-round enjoyment.

In addition to the beach itself, Rosewood Beach also has a lovely boardwalk and walking paths for those who want to explore the natural beauty of the area. The beach is easily accessible and offers restrooms, making it an excellent spot for a relaxing day outdoors. If you love the beach but want something a little quieter, Rosewood Beach offers a laid-back atmosphere just a short drive from downtown Highland Park.

7. Take a Bike Ride on the Green Bay Trail

The Green Bay Trail is a 5.5-mile-long trail that runs through Highland Park, making it a fantastic way to explore the town while enjoying some fresh air. The trail is perfect for cycling, running, and walking, offering scenic views of nature and local landmarks. Whether you’re taking a leisurely bike ride or going for a brisk walk, the Green Bay Trail provides a peaceful route through suburban neighborhoods and wooded areas.

This well-maintained trail is open year-round, making it a great activity no matter the season. The surrounding trees and natural beauty change with the seasons, providing a new experience each time you visit. It’s a wonderful option for those who love outdoor activities and want to explore Highland Park from a different perspective.

8. Attend a Concert at Ravinia Pavilion

Ravinia Pavilion, located just outside of Highland Park, is one of the premier music venues in the area. This outdoor venue hosts a wide range of concerts year-round, featuring everything from classical music to contemporary artists. The summer months are particularly popular, with the outdoor lawn offering a great spot for picnicking and enjoying music under the stars. Visitors can attend performances by renowned musicians, local bands, and world-class orchestras at this historic venue.

During the off-season, Ravinia Pavilion continues to offer a variety of performances indoors, providing opportunities for music lovers to enjoy concerts year-round. The venue is also home to the Chicago Symphony Orchestra, making it a central hub for the city’s classical music scene. If you’re looking for a unique cultural experience, attending a concert at Ravinia Pavilion is an unforgettable way to spend an evening in Highland Park.

9. Visit the Molly’s Cupcakes Shop

Molly’s Cupcakes is a charming local bakery in Highland Park that has earned a reputation for its delicious, whimsical cupcakes. Whether you’re craving a classic vanilla cupcake or a more adventurous flavor, you’ll find a variety of sweet treats to satisfy your cravings. The bakery also offers cupcakes with gluten-free and vegan options, making it a great place for everyone to indulge in something sweet.

In addition to their famous cupcakes, Molly’s Cupcakes also has a cozy atmosphere with a cute, vintage-inspired interior. It’s a wonderful spot to enjoy your treats while catching up with friends or family. If you’re in Highland Park, Molly’s Cupcakes offers a delightful experience for anyone with a sweet tooth, making it a must-visit destination.

10. Explore the Sunset Woods Park

Sunset Woods Park is a beautiful 26-acre park that offers plenty of opportunities for outdoor recreation. Whether you’re interested in hiking, picnicking, or playing sports, this park has something for everyone. The park features walking trails, open fields, and sports fields, making it a great destination for families and individuals alike. The spacious layout allows for ample room to explore, relax, and enjoy nature.

The park is also home to a variety of seasonal events and programs, providing year-round activities for residents and visitors. In the summer, you’ll find families enjoying picnics and sports games, while in the winter, the park’s trails are perfect for a peaceful winter walk. With its beautiful landscapes and wide range of activities, Sunset Woods Park is a fantastic spot for enjoying the outdoors.

What to do if you have kids?

Highland Park is a wonderful place for families with kids, offering plenty of activities that will keep children entertained. From nature walks at Rosewood Beach to picnics and sports at Sunset Woods Park, there are endless opportunities for outdoor fun. The Ravinia Festival offers family-friendly concerts, while the Chicago Botanic Garden provides engaging programs that allow kids to learn about nature. In addition to these outdoor activities, there are plenty of kid-friendly events, festivals, and community gatherings throughout the year. Highland Park truly has something for every age, making it a great destination for family trips.

Where can I find free events in Highland Park, Illinois taking place this weekend?

To find free events in Highland Park, Illinois, Planmyweekend.ai is a great tool to discover local happenings. From outdoor concerts to farmers’ markets and community festivals, Planmyweekend.ai provides easy access to free events in the area. Whether you’re interested in a free outdoor event or a family-friendly activity, simply visit the website, search for free events in Highland Park, and you’ll find exciting things to do without spending a dime. It’s the easiest way to make the most of your weekend in Highland Park.

Final Thoughts

Highland Park, Illinois, is a beautiful, vibrant town that offers something for everyone, no matter the season. Whether you’re strolling through its scenic parks, attending a concert at Ravinia Pavilion, or enjoying delicious treats at Molly’s Cupcakes, there’s always something to enjoy in this charming town. The mix of cultural events, outdoor activities, and family-friendly attractions makes Highland Park an ideal destination for anyone looking to experience the best of suburban Illinois. With so much to see and do, it’s a place worth visiting time and time again. Plan your next trip to Highland Park and experience everything this wonderful city has to offer!

Dejon Brooks
Author: Dejon Brooks

Dejon Brooks is an entrepreneur who founded Trend Watchers with his life savings. Aged 24, Dejon has turned Trend Watchers into a successful business. After reaching over 150M+ people on his personal accounts, he now spends his time growing Planmyweekend.ai

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