Portland is a winter wonderland, full of beautiful lights and potentially snowy sights. As the holiday season comes in quickly, and Portland receives many visits from friends and family, tourists and locals alike are wondering where they can go to experience the Portland festive scene. Below is a list of four walks, specialized for the cold season.
#1 – Mt. Tabor nature walk
This four-mile trail with hills showcases the beauty of the Jade District and the luscious Portland greenery. Highlighting the Water Bureau, Mt. Tabor Park and passing by Portland Community College, it’s perfect for the beginning of winter when the leaves are still falling. Be careful on rainy days – some sections of this walk don’t include sidewalks.
Start at the Portland Community College (PCC) Southeast Campus and walk west on Southeast Division Street until you reach SE 60th Avenue. Take a right onto SE Lincoln Street and continue on for about 0.2 miles before taking a right to Mt. Tabor Park. Take a left at the end of the street into the park and follow the main road through the park. Stay left at the first fork in the road, and right at the second fork to the park exit. Continue straight on SE 69th Avenue to SE Yamhill Street. Then take a right to SE 71st Avenue and another right to SE Taylor Street. Take a left on Taylor to SE 72nd Avenue and a right to SE Mill Street. Continue left to 76th Avenue and take another left to SE Market Street. Turn right onto SE 80th Avenue and take a right on SE Mill Street. Go left on Mill to SE 82nd Avenue and take a right to finally end up back on SE Division Street in front of the PCC Southeast Campus.

#2 – The classic downtown waterfront loop
This 2.6-mile classic downtown waterfront loop walk features a nice view of the Portland winter skyline, and can be extra pretty on a rainy or snowy day. Highlights include the Tom McCall Waterfront Park, the Steel Bridge, the Vera Katz Eastbank Esplanade and the Hawthorne Bridge to complete the loop. From Dec. 4 to 21, browse the schedules on the official Northwest Christmas Ships website for the Willamette River to catch a glimpse of the Portland Christmas Ships parade and the beautiful festive lights that line the waterfront.
Start at the Salmon Street Springs and walk north on the Willamette Greenway Trail for about 0.9 miles until approaching the Steel Bridge. Cross the Steel Bridge and take a right on the lower deck of the Steel Bridge, approaching Eastside Esplanade. Walk through Eastside Esplanade and its floating walkway for about a mile until you approach the Hawthorne Bridge. Take a left at the first northern ramp leading to the Hawthorne Bridge. Do not cross under the bridge! Take a right at the top of the ramp, and continue west across the Hawthorne Bridge. Turn right after crossing where the walkway splits, following the ramp to street level and Tom McCall Waterfront Park, and continue north back to the Salmon Street Springs.

#3 – Reed College walk
Get a nice glimpse of the Reed College campus and generations of Portland housing through this 3.5-mile walk through Southeast Portland. This walk is even better for prospective students who want to get a glimpse of Reed College, or even just what higher education in Portland could look like. Wear some walking shoes – not all sections of this walk are paved!
Start at SE Reed College Place and walk north until SE Woodstock Boulevard. Take a right on Woodstock to SE 41st Avenue and a left on 41st to SE Steele Street. Take a left on Steele to SE 36th Avenue and take a right on 36th, continuing until SE Raymond Street. Take a loop by going left on Raymond to SE 35th Avenue, and take a left on SE 35th Avenue to continue down SE Steele Street. Take a right on Steele to SE 28th Avenue and then take a left on SE Woodstock Boulevard. Go left to SE 32nd Avenue and take a right to SE Claybourne, and finish off your walk with a right to SE Reed College Place.

#4 – Nob Hill Loop
This simple walk through the Nob Hill area is a perfect short and sweet route to finish all of your holiday shopping. During the Christmas season, many of the shops are decked out in bright flashing lights, making the route all the more festive and scenic. It’s about two miles, not counting any shopping or food stops along the way!
This walk is straightforward and simple to follow. Start at the NW Mani & Pedi Nail Salon, and head north on NW 21st Avenue toward NW Everett Street for 0.8 miles. Turn left onto NW Thurman Street and take another left onto NW 23rd Avenue and continue for 0.7 miles. This will provide for a loop between the main shopping and food center of Nob Hill. Turn right onto NW Everett Street and finish off at Sunny Day Coffee & Pastry. Be sure to stop by for a warm coffee on a cold winter day.

