Outdoor Recreation

  1. Bike
  2. Camp
  3. Climb
  4. Paddle
  5. Trails & Paths


Bluffside Park Trail System

The Bluffside Park trail system contains over 10 miles of multi-use trails, providing picturesque views of the valley from the bluffs. Trail use is designated for mountain biking, hiking, skiing, and snowshoeing. Trails are available during all seasons. The trails feature winding curves and rolling hills, picturesque views and vary in difficulty. 

Lower trailhead and parking are available at Holzinger Lodge. Upper trailhead with a small amount of on-street parking is available on Wincrest Drive.

Bluffside Park Trail Map

Flyway Trail - Winona ConnectorPhoto of bike at sunset located on the flyway connector trail

The Flyway Trail - Winona Connector is a new trail linking Winona to Buffalo County, WI. The trail begins in Levee Park on Johnson Street, traverses the Highway 54 Interstate Bridge and the John A. Latsch Historical Wagon Bridge, as well as the new 842-foot bridge over the Burlington-Northern Santa Fe railroad.

Flyway Trail Winona Connector Map

The Flyway Trail Board has plans for expansion on the Wisconsin side to connect to the Trempealeau Wildlife Refuge and the Great River State Trail. For more information about the Flyway Trail, please visit the Flyway Trail Board's website: https://flywaytrail.com


Lake Park Path

Lake Winona Path is a popular destination for both visitors and local residents. The five-mile blacktop trail runs along the south side of the city and circles both segments of the lake through Lake Park. The route is flat and easy. This is a good place for families to ride or walk with children. Pedestrians, in-line skaters and cyclists use the path, so be alert. The trail provides excellent views of Lake Park, the surrounding bluffs and some of the city’s neighborhoods. Lake Winona trail is a great place to begin exploring the city and the area. 

  • Both East and West Lakes not using Huff Street: 5.3 miles
  • East Lake: 3.7 miles
  • West Lake: 1.8 miles
  • Bridge by the inlet to Vila Street: 0.4 miles

Bike Repair Stations 

The city of Winona provides four bike repair stations, available for use to the public. Map of Public Bike Repair Stations

Bike repair station

Bike Registration 

Bike registration is free for residents of the City of Winona through the Police department. For more information, visit Winona Bicycle Registration.