distance: 2.5 miles (4km)
time: Three hours plus museum/shopping time
START: Morse Museum
END: Cornell Fine Arts Museum
Points to note: The museums close Mondays.
Surrounded by large lakes, Winter Park was founded in 1881 as a winter resort for northerners. The Amtrak station and railroad tracks running through the heart of town are reminders that these early, wealthy visitors came by train.
As the citrus-growing business thrived, so did the town, and Winter Park developed a lifestyle of gracious homes and fine cultural institutions that remains today. Rollins College, an elite, private institution named for one of the city founders, is a liberal arts institution on a beautiful, serene campus.
Each year in March, the city hosts the Winter Park Sidewalk Art Festival. The three-day event is one of the most prestigious outdoor arts festivals in the country. More than 225 artists from around the world and 350,000–400,000 visitors attend. For more information, visit www.wpsaf.org.
In a world of ever-increasing chains, Winter Park also stands out for its high-quality, one-off shops and restaurants. Park Avenue, the main thoroughfare, has around 140 stores and galleries, as well as cafés, wine bars, and fine dining. It’s divided into a north and south part, with the center on Morse Avenue.
Street parking can be tough to find, but there is free all-day parking in lots of garages on Canton Avenue by the railroad tracks, and across the tracks on either side of Morse Boulevard at New York Avenue.
Shady Central Park
Julie Fletcher/Visit Florida
Charles Hosmer Morse Museum of American Art
The route begins at the Charles Hosmer Morse Museum of American Art 1 [map] (445 N Park Avenue; tel: 407-645-5311; www.morsemuseum.org; Tue–Sat 9.30am–4pm, Sun 1–4pm). From lamps to pottery, jewelry, paintings, and art glass, it contains the world’s most comprehensive collection of works by Louis Comfort Tiffany (1848–1933). An expansive wing added in 2011 features exhibitions tied to Laurelton Hall, the late artist’s Long Island, New York, home. Leaded glass windows, custom furnishings, and the architecture itself – plus the Fountain Court reception hall – are all on display.
A museum highlight is the Tiffany Chapel, designed by the artist himself for the World’s Columbian Exposition in Chicago in 1893. The Byzantine-style interior with its carved arches and intricate glass mosaics covering every inch of the pillars, altar, and baptismal font is simply stunning, while an enormous cross-shaped electrified chandelier hangs overhead. Free tours are available using your own mobile phone.
Tiffany lamps on display at the Charles Hosmer Morse Museum
Michael DeFreitas/roberthard/REX/Shutterstock
Park Avenue
Stroll south along Park Avenue. The eclectic range of stores and galleries is an invitation to browsing and window-shopping. A few to watch for include the Scott Laurent Collection (www.scottlaurentcollection.com), a gallery of contemporary art and furnishings; Synergy (www.synergysportswear.com), with a large collection of lifestyle clothing and comfort shoes; and Be on Park (http://beonpark.com), with designer jewelry and local art.
Park Avenue is often said to be European in style, with its cobbled street lined with sidewalk tables. But many of its two-story buildings look right out of 1920s America. A good place to fortify yourself with a coffee or ice cream is at the Briarpatch Restaurant, see 1, where tables with bright umbrellas are set across the street from a park with beautiful oaks draped in Spanish moss. If you’d prefer a craft cocktail, a glass of Italian wine, or Orlando’s best pasta, stop instead at the indoor-outdoor Prato, for more information, click here, for progressive Italian fare. Bosphorus, see 2, which serves Turkish cuisine, is a must for its puffy lavash bread.
On the opposite side of the street, shady Central Park 2 [map] with its flower gardens and bandstand adds to the village-like atmosphere. There are often free concerts here on weekends. The park stretches for several blocks, with the railroad tracks running along the western side.
Stores and galleries line Park Avenue
Julie Fletcher/Visit Florida
Scenic Boat Tour
Turn east down Morse Boulevard and follow it to its end at Lake Osceola. Here, the Scenic Boat Tour 3 [map] (312 E Morse Blvd; tel: 407-644-4056; www.scenicboattours.com; daily 10am–4pm) shows you Winter Park from a different perspective, with guides giving an entertaining commentary along the way. The one-hour cruise sails along three of the area’s chain of lakes and through the historic canals that link them; these were dug in the late 1800s for logging operations and today are solely used for pleasure boats.
After passing several gorgeous homes – many of these large mansions were mere summer retreats for wealthy families – you see the Albin Polasek Museum & Sculpture Gardens 4 [map] (633 Osceola Avenue; tel: 407-647-6294; www.polasek.org; Tue–Sat 10am–4pm, Sun 1–4pm). The Czech-American sculptor retired to this estate, and you can glimpse some of his works in the gardens. The museum contains many more of his paintings, drawings, and sculptures in addition to antiquities from his private collection.
The cruise then heads into the lush and overgrown Fern Canal which progresses into Lake Virginia. From here you can see some of the landmarks of Rollins College, looking very pretty and peaceful from the water.
Hannibal Square exhibit
Willie J. Allen Jr/Visit Florida
Hannibal Square
After the cruise, return to Park Avenue. Turn left and carry on to the end of Central Park, then turn right on New England Avenue. Across the tracks, opposite the park’s southwest corner, is the site of the Saturday farmers’ market. The small brick building alongside houses the Winter Park History Museum 5 [map] (200 W New England Avenue; tel: 407-647-8180; www.wphistory.org; Thu–Fri 11am–3pm, Sat 9am–1pm, Sun 1–4pm) with photographs, artifacts, and other exhibits on the community.
More boutique stores and restaurants line the next two blocks to Hannibal Square 6 [map]. This was the heart of the black community, who moved here in the 1880s to work in railroad and domestic-service jobs in the growing Winter Park community. A mural depicts a historic moment in 1887 when citizens crossed the railroad tracks to cast their votes and elected two African-American aldermen to Winter Park’s town council.
In the next block, the Hannibal Square Heritage Center 7 [map] (642 W New England Avenue; tel: 407-539-2680; www.hannibalsquareheritagecenter.org; Tue–Thu noon–4pm, Fri noon–5pm, Sat 10am–2pm) has exhibits, photographs, and oral histories gathered from members of the community, and hosts traveling exhibitions.
Colorful clothing at Cornell Fine Arts Museum
Alamy
Rollins College
Return to Park Avenue and continue south. A detour right along Lyman Avenue leads you to the Winter Park Welcome Center and Chamber of Commerce (151 W Lyman Avenue; tel: 407-644-8281; www.cityofwinterpark.org), where you can pick up some maps and information.
Park Avenue ends at the grounds of Rollins College. Founded in 1885, it is Florida’s oldest college. The attractive campus, with its original Spanish-Mediterranean-style buildings, spreads along the shores of Lake Virginia. Notice the Walk of Fame near the entrance, made of stepping stones gathered from places linked to famous historical figures.
Turn left on Holt Avenue and follow it to its end on the shores of the lake, where you can visit another of Winter Park’s leading cultural attractions. Cornell Fine Arts Museum 8 [map] (1000 Holt Avenue; tel: 407-646-2526; www.rollins.edu/cfam; Tue 10am–7pm, Wed–Fri 10am–4pm, Sat noon–5pm, Sun 1–5pm) has an excellent collection of European and American paintings, sculpture, and decorative art from the Renaissance to contemporary times, with changing exhibitions and artists’ talks.
Also on campus are the Annie Russell Theatre and the Knowles Memorial Chapel, connected by a loggia. Both buildings were built in 1931–2 and feature on the US National Register of Historic Places.
Food and drink
1 The Briarpatch Restaurant
252 N Park Avenue; tel: 407-628-8651; www.thebriarpatchrestaurant.com; $
A wholesome spot for coffee or ice cream, as well as full meals. Watch the passing scene from the sidewalk tables. Open daily for breakfast and lunch.
2 Bosphorus
108 S Park Avenue; tel: 407-644-8609; http://bosphorousrestaurant.com; $$$
Serving Turkish cuisine, this popular restaurant is open for both lunch and dinner.