10 Must-See Things to Do Year-Round in Winter Park, Florida

Key Takeaways

• Winter Park, Florida offers a delightful mix of outdoor activities, cultural experiences, and local events that make it an ideal year-round destination.
• From scenic lakes to historic landmarks, Winter Park is a hidden gem for nature lovers, history buffs, and art enthusiasts.
• Whether you’re exploring local parks, enjoying a gondola ride, or experiencing vibrant festivals, Winter Park provides a memorable experience for visitors of all ages.

Table of Contents

1. Visit the Winter Park Chain of Lakes
2. Explore the Charles Hosmer Morse Museum of American Art
3. Stroll Through Central Park
4. Take a Scenic Boat Tour
5. Check Out the Winter Park Farmers Market
6. Experience the Cornell Fine Arts Museum
7. Attend the Winter Park Sidewalk Art Festival
8. Walk Through the Mead Botanical Garden
9. Discover the Scenic Rollins College Campus
10. Enjoy a Day at the Winter Park Playhouse

Winter Park, Florida, is a picturesque city located just north of downtown Orlando, known for its beautiful lakes, charming streets, and rich cultural scene. Originally founded in the late 1800s, Winter Park grew from a winter retreat for wealthy Northerners into a vibrant community that combines both historical charm and modern attractions. Visitors love Winter Park for its lush green spaces, art galleries, and the delightful mix of outdoor and indoor activities that can be enjoyed throughout the year. Whether you’re looking for a peaceful lakeside stroll, an art-filled day, or an exciting cultural festival, Winter Park offers something for everyone.

1. Visit the Winter Park Chain of Lakes

The Winter Park Chain of Lakes is one of the most scenic and serene spots in the city, perfect for boating, fishing, and enjoying the outdoors. The chain consists of a series of interconnected lakes, offering beautiful water views and plenty of opportunities for water-based activities. Visitors can rent a kayak, paddleboard, or take a boat tour to explore the lakes and soak in the stunning surroundings. The peaceful environment and lush landscapes make it a great escape from the hustle and bustle, whether you’re looking to relax or engage in some active recreation.

Along the shores of the lakes, you’ll find charming parks and beautiful homes, adding to the area’s appeal. The lakes are also home to local wildlife, including birds and turtles, making it a perfect spot for birdwatching and photography. Whether you’re spending a few hours or the entire day, a visit to the Winter Park Chain of Lakes is a must-do activity for nature lovers and anyone looking to unwind in a beautiful setting.

2. Explore the Charles Hosmer Morse Museum of American Art

The Charles Hosmer Morse Museum of American Art is a cultural treasure trove located in the heart of Winter Park. The museum is home to an impressive collection of American art, including works by renowned artists like Louis Comfort Tiffany. The museum’s collection features stunning stained glass windows, jewelry, and decorative arts that highlight the beauty of American craftsmanship. Visitors can enjoy the vast exhibits, which cover a wide range of artistic styles and periods, from the late 19th century to the early 20th century.

In addition to its permanent collection, the museum hosts rotating exhibits and special events throughout the year. Whether you’re an art enthusiast or someone simply looking to explore the local culture, the Charles Hosmer Morse Museum provides a fascinating and enriching experience. The museum’s peaceful atmosphere and educational displays make it an ideal destination for anyone interested in American art history.

3. Stroll Through Central Park

Central Park in Winter Park is a vibrant green space that offers a peaceful escape right in the heart of the city. The park is a popular spot for both locals and visitors, offering walking paths, open lawns, and scenic views of the surrounding lakes. With its lush gardens and large oak trees, Central Park is the perfect place for a leisurely stroll, a picnic, or simply relaxing by the water. The park also hosts a variety of events throughout the year, including live music performances, movie nights, and holiday celebrations.

In addition to its natural beauty, Central Park is home to several statues and historical monuments, adding a cultural element to the area. It’s a wonderful place to spend the day, enjoy the outdoors, or participate in one of the many community events that take place throughout the year. Whether you’re looking to relax or take part in local festivities, Central Park is a must-visit spot in Winter Park.

4. Take a Scenic Boat Tour

A scenic boat tour is one of the best ways to explore Winter Park’s stunning lakes and waterways. These guided tours offer a unique perspective of the city, as you cruise through the Winter Park Chain of Lakes while learning about the area’s history and local wildlife. The boat tours pass by beautiful homes, historic landmarks, and lush landscapes, providing a peaceful and relaxing way to take in the sights. It’s a great way to see the city from a different angle while enjoying the fresh air and scenic beauty.

Boat tours are offered year-round, with knowledgeable guides who share interesting facts about the area’s history and natural surroundings. Whether you’re visiting for the first time or looking to discover more about Winter Park, a boat tour offers a fun and informative way to experience the city’s beauty. The tranquil atmosphere on the water is perfect for anyone looking to relax while exploring the charm of Winter Park.

5. Check Out the Winter Park Farmers Market

The Winter Park Farmers Market is a must-visit destination for food lovers and anyone looking to experience the local culture. Held every Saturday morning, the farmers market features fresh produce, locally made products, and delicious food from regional vendors. It’s the perfect place to grab a fresh snack, shop for unique handmade goods, or just enjoy the vibrant atmosphere. The market is located in the historic train depot, adding to its charm and creating a nostalgic feel for visitors.

Beyond the fresh fruits and vegetables, the farmers market also offers artisan breads, handmade crafts, and locally sourced honey and jams. It’s a great place to pick up ingredients for a homemade meal or find a one-of-a-kind gift. With its lively atmosphere and variety of offerings, the Winter Park Farmers Market is a great place to spend a Saturday morning and experience the local culture.

6. Experience the Cornell Fine Arts Museum

The Cornell Fine Arts Museum is a hidden gem in Winter Park, offering visitors a chance to immerse themselves in art and culture. Located on the Rollins College campus, this museum houses a diverse collection of art from the Renaissance period to contemporary works. With rotating exhibits and permanent collections, the museum provides something new for every visit. The museum’s collections feature paintings, sculptures, and prints, offering a deep dive into the art history of various cultures and time periods.

Beyond its impressive collections, the Cornell Fine Arts Museum also offers educational programs, lectures, and community events throughout the year. Whether you’re an art enthusiast or simply looking to experience some culture during your visit, the museum provides a welcoming atmosphere to enjoy the arts. The peaceful environment of the museum makes it an ideal place to reflect, learn, and appreciate art in all its forms.

7. Attend the Winter Park Sidewalk Art Festival

One of Winter Park’s signature events, the Winter Park Sidewalk Art Festival is an annual celebration that showcases the best in local and national art. Held in the heart of Winter Park, this festival features more than 200 artists displaying their work along the city’s charming streets. Visitors can explore a wide range of artistic mediums, including sculpture, photography, paintings, and jewelry. The event provides a unique opportunity to purchase original artwork while supporting local talent.

The Winter Park Sidewalk Art Festival also offers live music, food trucks, and activities for all ages. It’s a family-friendly event that draws large crowds every year, creating a lively and festive atmosphere in the city. Whether you’re an art lover, a casual visitor, or someone just looking to enjoy a fun weekend out, the Sidewalk Art Festival is an event you won’t want to miss.

8. Walk Through the Mead Botanical Garden

The Mead Botanical Garden is a peaceful retreat located in the heart of Winter Park, offering visitors a chance to immerse themselves in nature. The garden spans over 40 acres and features beautifully landscaped areas, including butterfly gardens, wetlands, and natural woodlands. Visitors can enjoy walking through the garden’s diverse ecosystems, which are home to many native plants and wildlife species. The serene environment is perfect for a relaxing stroll or a quiet spot to meditate and enjoy the outdoors.

In addition to its natural beauty, the Mead Botanical Garden also hosts educational programs, volunteer opportunities, and seasonal events. It’s an excellent place for nature lovers, photographers, and anyone looking to spend time outdoors. Whether you’re taking a leisurely walk or attending a garden workshop, Mead Botanical Garden offers a peaceful escape from the bustle of city life.

9. Discover the Scenic Rollins College Campus

Rollins College, located in Winter Park, is one of Florida’s most scenic college campuses, with its lush green spaces and stunning views of Lake Virginia. The campus is home to beautiful Mediterranean-style architecture and historic buildings, making it an ideal spot for a relaxing walk. Visitors can enjoy the calm atmosphere while admiring the well-maintained gardens and picturesque views of the lake. The campus also features a number of outdoor sculptures and public art installations, providing a blend of nature and culture.

Rollins College frequently opens its doors to the public for events such as concerts, theater productions, and lectures, making it a vibrant cultural hub in Winter Park. Whether you’re attending an event or just taking a casual walk around the picturesque campus, Rollins College is a must-see during your visit to Winter Park.

10. Enjoy a Day at the Winter Park Playhouse

The Winter Park Playhouse is a lively venue that offers year-round entertainment for theater lovers. This intimate theater features a variety of performances, including Broadway-style musicals, local plays, and special events. The playhouse’s small size creates an up-close and personal experience, allowing you to enjoy every detail of the performance. Whether you’re a fan of classic musicals or new performances, the Winter Park Playhouse provides high-quality entertainment in a welcoming setting.

In addition to its regular performances, the Winter Park Playhouse offers educational opportunities such as acting classes and workshops for aspiring performers. It’s the perfect destination for those looking to enjoy a night of live theater in the heart of Winter Park. With its commitment to the arts and community involvement, the Winter Park Playhouse is a true cultural asset to the city.

What to do if you have kids?

Winter Park is a wonderful destination for families, with plenty of activities that cater to children. The Winter Park Boat Tour is a great option for kids to enjoy a scenic ride on the lakes, learning about the area’s history while spotting local wildlife. Central Park, with its playgrounds and open spaces, is perfect for letting kids run around and enjoy some outdoor fun. The Mead Botanical Garden is another family-friendly destination, where children can explore the natural world and enjoy the peaceful surroundings. With its combination of educational, outdoor, and fun activities, Winter Park offers a range of experiences that kids will enjoy.

Where can I find free events in Winter Park, Florida taking place this weekend?

To find free events in Winter Park this weekend, check out Planmyweekend.ai. This tool allows you to easily discover local happenings, from free outdoor concerts and festivals to community markets and educational events. Whether you’re looking for something to do with the kids or enjoying an afternoon outdoors, Planmyweekend.ai makes it easy to find the best free activities in Winter Park. Simply visit the website to plan your weekend and explore all that Winter Park has to offer without spending a dime.

Final Thoughts

Winter Park, Florida, offers a fantastic blend of outdoor activities, cultural experiences, and community events that make it a must-visit destination. From the scenic lakes and botanical gardens to the vibrant arts scene and historic landmarks, there’s something for everyone to enjoy year-round. Whether you’re looking to explore nature, enjoy local art, or relax in beautiful parks, Winter Park provides an unforgettable experience for visitors of all ages. Plan your trip to Winter Park today and experience everything this charming city has to offer!