Unwrap the Holidays with Highland Park Attractions

Art Center of HP

The art center provides residents and visitors alike with art classes, workshops, exhibitions and dozens of community events. Stroll through the museum-like galleries with ever-changing of creations concocted by local, international, emerging and established artits. While they will host a few workshops throughout the holiday season, view their Nov. 6-Dec. 12 exhibit "Unfamiliar Patterns" featuring the work of Eleanor Spiess-Ferris and Michael Ferris, while December 18-January 29, the center hosts the annual members and faculty show. 

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Centennial ICe Arena

The Park District of Highland Park facility features an indoor ice rink and a fully-equipped gymnastics studio. They offer public skating as well as Learn to Skate, hockey, freestyle, and gymnastics lessons for all skill levels. Centennial offers public skates throughout the holiday season.

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Danny Cunniff Park

The Park District of HP park is equipped with a playground, tennis courts, walking paths, baskeball courts and so much more if you're looking to brave the storm with a little running room for the kids during the holiday season. The facility is also home to Centennial Ice Arena. Let's not forget about the gigantor hill for sledding if the snow falls enough. This hill is located just south of the Park District of Highland Park's Centennial Ice Arena. Sliders are encouraged to stay within the fence as there are no supervision or warming facilities to the sled hill.

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Downtown Highland Park

Downtown Highland Park is the heart of the North Shore, and during the holidays it becomes an especially festive place to gather, shop, and celebrate. The Park District of Highland Park brings the season to life with wintry lakefront views, cozy outdoor spaces, and seasonal recreation for every age. For a night of holiday cheer, Wayfarer Theaters offers live entertainment that makes the perfect addition to any seasonal outing. Just a short drive away, Lynfred Winery invites guests to warm up with tastings in a historic setting, ideal for toasting the season with friends and family. Diners can explore a wide range of flavors, from the bold, authentic dishes at Indus Progressive Indian to the locally minded fare at Steep Ravine. Backyard Grill serves up a casual, crowd-pleasing menu that’s great for relaxed holiday get-togethers, while Central Cafe is a cozy stop for a warm drink and a bite between errands. Braeside Market adds gourmet touches and a distinctly local feel, making it a wonderful place to find ingredients and treats for your own holiday table. Port Clinton Square anchors the downtown experience with boutiques, specialty shops, and dining, all within an easy stroll and perfect for finding that one-of-a-kind gift. Whether you’re checking names off your gift list, planning a festive date night, or simply soaking in the sparkle of the season, Downtown Highland Park delivers a warm, welcoming holiday experience in one memorable destination.Kick off the season at the Holiday Lighting ceremony at Port Clinton Square on Saturday, November 21, from 4 to 6 p.m., then come back on Small Business Saturday, November 28, to shop local, find one-of-a-kind gifts, warm up with a bite or a drink, and support the independent businesses that make area sparkle.

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Heller Nature Center

This wooded escape is rich in winding trails, towering oaks and serene vibes. During fall, the canopy becomes a kaleidoscope of warm tones. It’s perfect for moody, nature-lover portraits or simple leaf-crunching/snow sauntering stroll shots. Throughout the season, the Park District of Highland Park entity offers a ton of themed activities like:

• Saw-whet Owl Banding (Nov. 6) 
• Nature Play Date (Nov. 7) 
• Arctic Adventure: Stories and Crafts (Dec. 9) 

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Lynfred Winery

llinois' eldest winery is Lynfred, established 42 years ago in 1979. Founded by Fred E. Koehler, whos also known as the father of the Illinois wine industry. From its 100,000-gallon production facility to its luxurious bed-and-breakfast accommodations, Lynfred has become a Chicagoland icon for wine enthusiasts. The Lake County vino tasting room has been earning awards and national recognition since 1985. The winery also was named as a part of the Illinois Made program, by the Illinois Office of Tourism. Lynfred Winery in Highland Park invites visitors to try its cranberry wine, made from 100% Wisconsin-grown cranberries. Bold and bright, the wine balances natural sweetness with refreshing acidity. Flavors of cranberry, wild berries and plum come together in a medium-bodied wine with a crisp, clean finish. This versatile wine is good on its own, as a sparkling spritzer or paired with seasonal desserts, tarts and cheeses. Its lively character and holiday-ready flavor make it a standout choice for winter sipping. 

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Park District of Highland Park

From the beach to the nature preserves, to the ice arena and so much more, the North Shore's park district has a slew of activities and happenings throughout the holiday season. Heller Nature Center, West Ridge Community Center, Rosewood Beach, Centennial Ice Arena, Jens Jensen Park and the Preserve of Highland Park are all properties of this bustling park district. From turkey trots, to cookie and cocoa crawls, to scooting along the ice during public skate and exploration during winter break, Park District of Highland Park is your one-stop shop for holiday affairs. 

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Prairie Wolf Forest Preserve

Prairie Wolf is a photo playground, offering fields of tall grasses swaying in autumn/winter hues. The wide-open skies make it easy to catch golden-hour shots that glow. Bonus points if you bring your pup—the off-leash area is full of action shots waiting to happen. The LCFPD property is highlighted by a 20-acre wetland, a 1.75 mile trail for hiking, biking and cross-country skiing and a one mile self-guided nature trail. 

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The Preserve of Highland Park

The Preserve of Highland Park located adjacent to the Recreation Center of Highland Park opened to the public in June 2022. This unique natural area for passive recreation includes green lawns, nature-based play areas, specialized native gardens, restored woodlands, and walking and biking trails that connect neighborhoods, downtown Highland Park, and regional biking trails. Visitors can immerse themselves in the sights, sounds and experiences of nature and outdoor play. Even during the holiday and winter seasons, it is a spectacular area to take a stroll, birdwatch and just get away from it all with some peace and quiet. 

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Ravinia Festival | Bennett Gordon Hall

Ravinia is a staple of Lake County. Since 1905, the Highland Park fest has featured the top musicians from myriad genres, making it the oldest outdoor festival in U.S. history. Like every year, Ravinia showcases a slew of star-studded acts like John Legend, Carrie Underwood, Ms. Lauryn Hill, Chicago, Santana, Buddy Guy, Brandi Carlile, Train the Chicago Symphony Orchestra and so many more. During the holiday season, they bring the live tunes indoors indside the Bennett-Gordon Hall. During the holiday season, you can witness 

• Chanukah: Songs of Light (Dec. 2) INFO»
• Christmas with Cantus (Dec. 3) INFO»
• Wonderful: A Soulful Celebration (Dec. 4) INFO»
• A Merry Christmas with Dallas Brass (Dec. 5 ) INFO»
• Jingle Bell Jam! Featuring the JAM Orchestra (Dec. 6) INFO»

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Rosewood Beach and INterpretive Center