Oak Park’s holiday events and activities make the neighborhood a festive destination to celebrate the season, bringing together food, family fun and a vibrant community atmosphere. Whether you’re looking for family activities, holiday shopping or simply a taste of holiday spirit, Oak Park always has something to explore.
Holiday Housewalk & Market
The experience: This festive event on December 6-7 lets participants tour beautifully decorated homes, showcasing diverse holiday styles. In addition, visitors can browse the holiday market for artisan crafts, décor and unique gifts.
Ideal for: Families, couples or friends looking to gather decorating inspiration and do some holiday shopping in a cozy, community-focused setting.
Winterfest & Cookie Walk
What to expect: For $30, participants receive a signature cookie tin and a map to collect a variety of cookies from local businesses. The event runs on December 7 from 10:00 AM to 3:00 PM—perfect for strolling through decorated streets and sampling local treats.
Pro tip: Tins sell quickly, so reserve early for a guaranteed spot on this sweet tour of Oak Park’s holiday spirit.
Home for the Holidays
What’s happening: On December 21, festivities will start at 9:00 AM with a free holiday movie at the Lake Theatre. Families can enjoy horse-drawn carriage rides from 11:00 AM – 2:00 PM and meet Santa while sipping complimentary hot cocoa at participating shops.
Don’t miss: Live holiday music will be performed throughout the area from 12:00 PM – 3:00 PM, creating a festive soundtrack for holiday shopping and mingling.
Frank Lloyd Wright Home and Studio
Why it matters: Frank Lloyd Wright revolutionized modern architecture. The cool part? He laid the foundation for his groundbreaking designs right in Oak Park! The home and studio, where Wright lived and worked between 1889 and 1909, offers a unique glimpse into his early works and creative process.
Details: The tour showcases Wright’s Prairie-style architecture, characterized by horizontal lines and open floor plans. This area boasts the highest concentration of Wright-designed buildings anywhere in the world.
Go deeper: The home is not only an architectural masterpiece but also a National Historic Landmark. It’s a must-visit for architecture enthusiasts and history buffs alike.
Ernest Hemingway Birthplace Museum
Why it matters: Ernest Hemingway, one of the greatest American writers, was born in Oak Park in 1899. His former home is now a museum, offering visitors insights into the formative years of the literary legend.
Details: The museum features original furnishings, Hemingway family artifacts and exhibits that detail his early life and career. Visitors can also explore the nearby Ernest Hemingway Museum, which complements the birthplace with a deeper dive into his legacy.
Don’t miss: A visit to the museum will provide a full picture of Hemingway’s Oak Park roots and how the village influenced his world-renowned literary career.
Pleasant Home
Why it matters: This stunning Prairie-style mansion, designed by George W. Maher in 1897, represents a prime example of American residential architecture from the turn of the 20th century.
Details: Known for its intricate craftsmanship, the house features grand rooms, ornate woodwork and art glass windows. It’s now a museum and cultural venue that offers guided tours and hosts various cultural programs.
What to know: Pleasant Home is a National Historic Landmark and often features art exhibitions, performances and community events.
Oak Park Conservatory
Why it matters: Oak Park Conservatory is a tranquil urban escape. It offers a vibrant collection of exotic plants and lush indoor gardens in the heart of the village.
Details: Established in 1929, this conservatory houses three distinct biomes: tropical, Mediterranean and desert. Visitors can explore the flora in each, and the conservatory also hosts educational programs and seasonal plant sales.
Go deeper: This serene spot is ideal for families and nature lovers looking to enjoy a peaceful environment year-round. You can even enjoy it in the colder months.
Austin Gardens
Why it matters: This peaceful park offers a green retreat within Oak Park, with beautiful landscaping, shaded areas and cultural events that highlight the village’s love for the arts.
Don’t miss: The outdoor theater events, particularly Shakespearean performances, are a highlight during the warmer months
Details: Austin Gardens provides space for leisurely walks, picnics and community activities throughout the year.
