Your Guide to Romantic Winter Hikes This Valentine’s Day

Wander local trails this February and get your heart pumping.

ONE OF THE MOST enjoyable aspects of living in Milwaukee is access to an abundance of trails and natural spaces throughout the city and surrounding areas, many of which remain accessible throughout winter. With the right winter gear, these spaces can be enjoyed with friends, family, solo or with someone special, if they are fond of outdoor adventure. Have a new love interest, or looking for something exhilarating to do with your old flame on Valentine’s Day week? Check out some opportunities for getting out there for a romantic winter hike. 

1. Lakeshore State Park


This state park on the edge of the Third Ward provides a loop of paved paths through native grasses, a lagoon, one rugged trail right up against the shoreline, beautiful lake and city vistas – and memories of Summerfests  past to spark conversation. Warm up afterwards in the Third Ward, at the Milwaukee Art Museum, or Harbor House. Park on the street near the north lawn adjacent to the SummerFest grounds, or on the park’s south side. Lakeshore State Park closes at 10 p.m. 

2. Havenwoods State Forest


Described on its website as “Wisconsin’s only urban state forest,” the area boasts six miles of flat trails through wood and marshland, so you can get lost, without actually getting lost. The nature center offers a Geocashing trail guide, if you’re into that. Warm up in the nature center, and take advantage of ample parking onsite. Havenwoods State Forest closes at 8 p.m.



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3. Humboldt Park


This 70+ acre county park is made up of paved trails that weave up and down gently sloping hills through mature trees, providing plenty of territory to cover during conversation. Swing by the lagoon and hit the ice for some of the finest ice skating in the area (but be sure to check conditions online, first). Afterward, stop into Lakeside Bakery for a treat and to warm up. Make use of ample street parking within the park. Humboldt Park is supported by membership and closes at 10 p.m.

4. South Shore Park and Bay View Park

2900 SOUTH SHORE DR. & 3120 S. LAKE DR.

Two other Bay View county parks are adjacent to one another, and collectively offer gorgeous harbor, lake, and city views. Take the lake path from the pavilion all the way to the Archdiocese of Milwaukee. Walk the beach for part of the way, which has a bounty of lakestones and a makeshift driftwood pergola. If you’re in need of a warm up afterwards, it’s just a short drive to At Random. Parking is available in the north section of South Shore Park outside the pavilion, or on Lake Drive next to Bay View Park. These and other county parks are supported by donations to the Milwaukee Parks Foundation. South Shore and Bay View Parks close at 10 p.m. 

5. Grant Park


Grant Park, another Milwaukee County Park, offers some of the best trails and lake vistas around, including a segment of the Oak Leaf Trail. The Forked Aster Hiking Trail offers breathtaking lake views from the wooded bluff high above the shoreline. Parking is available at the Seven Bridges Park trailhead. Grant Park closes at 10 p.m. 

6. Lynden Sculpture Garden


Just north of the city is the former estate of Harry and Peg Bradley, 40+ acres of grounds that are home to an impressive array of large contemporary and Modern sculptures, including works by Barbara Hepworth, Charles Ginnever, Forest Myers, and works by local artists including Richard Galling and Michelle Grabner. As there are not groomed trails, be prepared to take in the sculptures without a prescribed path. Warm up inside the house, and find parking in the large parking lot on the grounds. Access is free to the public at this time. Lynden Sculpture Garden is supported by membership, and closes at 5 p.m. 

7. Ice Age Trail: Eagle Segment 


Located in Waukesha County, this segment of the Ice Age Trail is worth traveling a little further afield for. This portion of the Trail is part of the Kettle Moraine South Forest, with a path that passes in and out of thickets of poplar, hickory and oak trees and wild grass prairies. The trail offers an elevation with a scenic lookout, and benches are periodically positioned along the path. Park at the wayside trailhead. The Ice Age Trial Alliance is supported by membership. The trail closes to day users at 8 p.m. 

8. Kohler-Andrae State Park 


Located in Sheboygan, this state park offers picturesque views of Lake Michigan and a nature walk. Hike on portions of the dune cordwalk, or brave the beach itself and take in the sights of the dramatic ice dunes that line the shore. For a more protected stroll, take the nature trail loop on the south side of the park, which passes through a forest populated with large pine trees, and features tree identification cards. Kohler-Andrae State Park closes at 11 p.m.

Tips for Cold Weather Hiking:

  • Wear proper hiking boots. Though trails may be partly cleared, packed or black ice can create hazardous conditions. 
  • In snowy conditions, use skis or snowshoes to experience ungroomed trails. Members can rent snowshoes, skis and poles from the Urban Ecology Center. 
  • Don’t neglect to bundle up with all the necessary gear, including long johns. There’s nothing fun about being unprepared for the elements. 

HOT TIP: Pack travel mugs, and a thermos of tea or something warm to share.