The Milwaukie Old Town Loop Hike includes a pleasant stroll through downtown Milwaukie and a stretch along the Milwaukie waterfront along the Willamette River. There are opportunities to grab a drink or a nice meal at local Milwaukie restaurants such as Cha Cha Cha or Casa de Tamales. Shopping and other activities include antique shops, a specialty chocolate shop, and a nickel arcade with a movie theater and a mini-golf course for those with children.
The section along the waterfront provides a nice breeze as you watch the Willamette River’s traffic, including both speedboats and many paddle boats. This section easily connects to the Trolley Trail Hike, which leads up to the beginning/end of the Milwaukie Max Orange line. Those with dogs will appreciate the dog park that is along the waterfront, and those looking to explore the river more can connect the trail to the Elk Rock Island Hike as well.
Because the trail is mainly an urban hike with a paved pathway and little elevation gain, it is very kid and pet friendly. The Old Town Loop can be tailored to the needs of each hiker, possibly being a nice afternoon walk that includes a meal at a local restaurant, or being a longer walk to include walking along the Willamette and to Elk Rock Island. During the summer season there is a busy farmer’s market every Sunday from 9:30 in the morning until 2:00 in the afternoon. The market often includes live music, local crafts and food, and of course fresh farmed produce and meats for sell.
Because the path is mainly downtown, you can set out on the Milwaukie Old Trail Hike wherever is best fit for your needs. You can either find parking in downtown Milwaukie and pick your path beginning at the waterfront in the parking area (though often this parking lot is filled with trucks with boat trailers), or you can park in the Orange Line Max Park and Ride parking lot and take the Trolley Hike Trail to the waterfront to begin the loop. To do the latter option, park in the Trimet Max Park and Ride parking lot and walk south, next to the Orange Max Line along the paved path. This section is the Trolley Trail and leads down to the waterfront along the Willamette River.
Once you come upon the waterfront area to the Willamette River, follow the paved path or walk down closer to the river. There are many routes to take, one being to continue along the waterfront park until you come to the intersection of Harrison Street and McLoughlin, along the northern tip of the waterfront park. Turn right on Harrison to cross McLoughlin and enter into downtown Milwaukie. Walking east along Harrison Street, most of the downtown area will be to your right (south). Take a left at Main Street, the first intersection, for a block, and then turn right directly after moving past SE Scott Street. This takes you to Scott Park.
Turn Right at Scott Park to follow SE 21st Ave., and then turn left again on Harrison Street. Following Harrison until turning left on SE 23rd Ave., you will walk past new high-rise apartment complexes. Turn right on SE Llewellyn St. and then right on SE 24th Ave. to reconnect with Harrison. From here, follow Harrison past the Portland Waldorf School back towards downtown. Take a left on SE 21st Ave. to head into the downtown proper area. Here there will be the chance to grab food from local restaurants as well as shopping options, coffee shops, and pubs. From 21st Ave., take a right on Monroe St., and then a left on Main Street to stay along the map’s path. Follow Main Street past SE Washington Street to head towards the downtown Max station, which has a nice set of food carts and a beer garden next to it. Otherwise, head right on Washington to head back towards Milwaukie’s waterfront.
In addition to the wonderful park along the river, downtown Milwaukie offers fun shopping opportunities and restaurants. In the summer they host a wonderful Farmer’s Market every Sunday including local crafts and food. If looking for antiques and collectables check out Main Street Collectors Mall and Soda Fountain along Main Street, Stars Antique Mall on SE Milwaukie Drive, or The Warfront on McLoughlin for military antiques and firearms. Wunderland Nickel Arcade also has a location in downtown Milwaukie that includes arcade games, a movie theater, and a mini-golf course for those traveling with kids. Those looking for local food and drink should check out Cha Cha Cha or Casa de Tamales for Mexican cuisine, Duffy’s Irish Pub for pub food or a drink, Gramma’s Corner Kitchen for breakfast and lunch, Rice Thai Cookery, or Ohana Hawaiian Cafe for a kid-friendly restaurant including shaved ice. Just north of the Trolley Trail/end of the Orange Line Max Station is also a kid-friendly diner, The Bomber, offering large portions of American diner classic meals.
The history of Milwaukie begins with the Clackamas tribe, who inhabited the shores of the Willamette River for thousands of years before the official designation of the Oregon Territory. In 1805, Lewis and Clark estimated the Clackamas People’s population to be around 1,800. In 1829 the ocean-bound ship, Owyhee, would bring Malaria to the area, killing 9 out of 10 of the Native Clackamas People.
By the late 1840s and early 1850s, settlers from the Oregon Trail arrived to the area, establishing lumber mills and fruit orchards. Despite these developments, Milwaukie eventually lost out on the competition to become the major city along the Willamette to Portland by the 1860s. Milwaukie was a semi-isolated area dependent on a river ferry and rough wagon trails to connect to Portland trading posts and other communities.
Flashing forward to the 21st century, Milwaukie has transformed into an urban center connected closely to Portland, Oregon. The city’s population growth has brought more people and money to the area, allowing for housing and business development. In 2015 the completion of the Orange Max Line provided public transportation connecting Milwaukie to Portland’s metro area. The Max is a popular means of commuting for Milwaukie residents working or studying in downtown Portland.