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Reported: May 2020

Winter Park Biking...

A City of Parks, Arts and Culture

Winter Park in Orange County (north of Orlando), developed in the 1880's as a resort community for wealthy northern business magnates, today is a thriving suburban community. Home to Rollins College, Winter Park's Park Avenue is a hub welcoming residents and visitors with restaurants, shops, museums, churches, historic and civic buildings, scenic Central Park, plus a golf course and cemetery. Nestled among several lakes (the Winter Park Chain of Lakes), there are boating and paddling launches and a popular scenic boat tour. While not a biking destination, many neighborhoods are bikeable, and the city is working to be more bike- and pedestrian-friendly through its transportation planning process. Shared-use paths have been developed, bike lanes and sharrows marked. (Map and photos below).

Winter Park Shared-use Trail

Winter Park Area Biking Map


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Location: Orange County (Winter Park)
Mileage: Various
Surface: Paved multi-use path, sidewalk, street
Trailheads/Parking: Blue Jacket Park, Azalea Lane Rec Center, Martin Luther King Jr. Park, Mead Gardens (See map)
Nearby Points of Interest: Park Avenue, Morse Museum of Art, Rollins College, Albin Polasek House and Gardens

Bike Shops / Bike Rentals:

Winter Park Cycles (Baldwin Park, Orlando; sales, service)

REI Co-op (Winter Park; sales)

Ace Metric Cycles (Orlando, Baldwin Park; sales, service)

Biking in Winter Park, Florida... Comments and Photos

We visited several sections of Winter Park, viewing various aspects of the city from lakeside to roadside. City streets are open to bicycles, but due to lack of dedicated trails biking on the sidewalks is sometimes necessary - allowed, unless posted (you can't bike on the sidewalk along Park Avenue, for instance). Other area trails can be accessed from Winter Park, providing a fuller bike experience on the Cady Way Trail, Lake Baldwin Trail, and Orlando Urban Trail.

Here we biked a route starting from Blue Jacket Park (in Orlando at Winter Park city limit), looping clockwise to Winter Park and return (about 6.5 miles). The route includes shared-use path, sidewalk, bike lanes, and on-road. The downside: many road crossings, business and residential driveways. Disclosure: We biked this route on a Sunday, the roads can be busier on weekdays and require extra care. There are many other routes available, and lovely parks and neighborhoods to visit plus the Park Avenue district - much to see and do in Winter Park!


Blue Jacket Park to Azalea Lane Rec Center

From Blue Jacket Park on General Rees Ave., go west on Glenridge Way - there's a bike lane, but it ends at Laurel Rd. - we rode on the wide sidewalk as did several others we passed. After about 4/10 mile, turn right at Winter Park Road where a shared-use path is on the west side of the street. Continue 1/4 mile where the path turns left at Lake Sue Ave. (which becomes Pennsylvania Ave.). It's about a mile to Azalea Lane Rec Center, turn left at Melrose (as we did, riding 2 blocks on the quiet street), or left at Minnesota Ave. and ride on the sidewalk 2 blocks to the Center (parking, restrooms, playground, tennis). Be watchful of driveways and road crossings.


Denning Drive Shared-use Path

From Azalea Lane Rec Center, we rode on the wide sidewalk (there's also a bike lane) along Minnesota Ave. to Orange Ave. and crossed to Denning Drive. This is a busy, 6-way intersection - use the crossing signals here for safety. The Denning Drive shared-use path was built as part of a road redevelopment project, and runs north about a mile to Webster Ave. passing Martin Luther King Jr. Park, Valencia State College (Winter Park campus), and Winter Park Village (shopping, restaurants). This parallels popular Park Avenue (shopping, restaurants, Central Park, Morse Museum of Art), which is about 1/2 mile to the east via bikeable cross streets. Take care on streets, at driveways and road crossings.


Denning Drive to Fairbanks Ave.

From the end of Denning Drive shared-use path, we biked a random route back to start, selecting mostly less traveled streets or using the sidewalks. We rode on the wide sidewalk along Webster Ave. to Pennsylvania Ave., riding on the sidewalk to Swoope St. where we rode in the street to Virginia Ave. Continuing riding in the street, we linked to the New York Ave./Fairbanks Ave. off-road connector along the railroad track, then a couple of blocks along Fairbanks Ave. (there's a bike lane, but we used the sidewalk) to New York Ave.


Fairbanks Ave. - Return to Blue Jacket Park

Crossing Fairbanks Ave. onto New York Ave. and to French St. Here we passed Rollins College and continued along Lakeview Drive - it's a brick street so bumpy, but a scenic neighborhood along Lake Virginia. We turned off at Stirling Ave., to Richmond St., returning to the Pennsyvania Ave. shared-use path and back to start.


Blue Jacket Park

Blue Jacket Park includes the former parade ground for the Orlando Naval Training Center once located here at today's Baldwin Park. The park has parking, restrooms, a shared-use path, playing fields, plus a Naval History wall and monuments outlining the naval history of the site. Although located in Orlando, we include it here because: (1) it's a convenient parking spot at Winter Park city limits, and (2) it creates a link to both the Lake Baldwin and Cady Way Trails. Follow the path through the park to Lake Baldwin Trail, then around Lake Baldwin to the link to Cady Way Trail (see map).

Links to Area Trails

Cady Way Trail

At its eastern border, Winter Park touches on the Cady Way Trail.

Cady Way Trail, Orlando biking
Visit Cady Way Trail

Lake Baldwin Trail

From Blue Jacket Park to Lake Baldwin Trail, link to Cady Way Trail.

Baldwin Park, Orlando biking
Visit Lake Baldwin Trail

Orlando Urban Trail

Through Mead Gardens, follow the path to the Orlando Urban Trail.

Orlando Urban Trail, Orlando biking
Visit Orlando Urban Trail

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