1. Lovejoy Fountain Park 

Start out at one of Downtown’s most beloved park fountains that gets popular during the summer, and if you’re lucky it will be frothing with bubbles that an enterprising youngster put in for giggles. Portland is full of fountains for those rare sunny days and this is one of the best ones. Continue walking down College Street towards the Park Blocks.

2. Park Blocks & Farmers Market

The first thing people usually notice coming to Portland is how green it is and downtown is no exception. The South Park Blocks run through Portland State University and up through several blocks providing a place with gardens, trees, and benches for shaded strolling.

The PSU Farmers Market is open year round, and also the largest in Portland with over 100 different stalls. Its hours are 8:30-2:00 PM Saturdays March-October and 9:00-2:00 PM November-February.

3. Portland State University Library

Look familiar? The Portland State Library which is also open to the public has been featured in the hit show Portlandia. Walking down Park Avenue you’ll pass several different older halls, dormitories, and a modern apartment building called the Vue (not important, but it was my first place living away from my parents at age 18-19!). Continue down the blocks until you reach the Portland Art Museum.

4. Portland Art Museum

Portland Art Museum and directly across the street, is the Oregon Historical Society Museum. About a block down is the Theater district with Arlene Schnitzer Concert Hall and Newmark Theater. Big names usually come here for comedy, speeches, and concerts. As you exit the Park take an immediate right on Salmon Street, on the corner of Salmon and Broadway (one block) you’ll find the historical Heathman Hotel, featured in the novel “50 Shades of Grey.” Continue down Broadway two blocks and explore Pioneer Courthouse Square.

5. Pioneer Square

Nicknamed “Portland’s Living Room,” Pioneer Square has plenty of free events including a gigantic Christmas tree during the holidays, summer farmers markets (Mondays 10 AM-2 PM), and Friday evening movies. If there isn’t an event during your visit there is always good people watching! Try to find your hometown or a favorite destination on the multi destination direction post. The three modern glass buildings that have connecting tunnels are the Pioneer Square Mall with typical retail stores and a food court.

Turn left onto Washington Street passing several historical hotels, O’Bryant park, and one the largest food cart pods downtown. One of Blue Star Donut’s locations is on the corner of 13th Street and Washington Avenue. One of Portland’s age old debates is argue about if Blue Star or Voodoo make better doughnuts so if you’re a doughnut connoisseur make sure to stop here, otherwise skip and head two blocks North to NW Couch street.

6. Pearl District Brewery Blocks

Burnside, NW Couch, and Davis streets are also known as the “Brewery Blocks” where three historical buildings (Portland Armory, Chevrolet dealership, and the Blitz-Weinhard Brewery) were preserved and renovated into multi-use buildings that stand today. There is ample shopping, dining, and modern breweries in this area as well.

7. Powell’s City of Books

Hours- 9 AM-11 PM daily

This is the largest used and new bookstore in the world- so large that they have over one million books, and a store map located at the information desks is highly recommended to navigate the color coded rooms on the multiple levels. Don’t miss the Weird display of the most random books the store associates could find on one bookshelf!

8. Chinatown & Voodoo Doughnuts

Portland has an official Chinatown, and this block containing the Chinese Garden, a few restaurants and the Hung Far Low sign is about the extent of it.  While walking down Burnside you’ll see the Paris Theater- it used to be a long running pornhouse and sex club, but recently (2016!) was converted into a music venue. There’s other music venues and clubs in this area- the Roseland and Wonder Ballroom. You may see a line out the door and a large pink “Voodoo Doughnuts” sign and you’ve arrived at the ORIGINAL location that is open 24/7 (except major holidays).

9. Portland Saturday Market & the Waterfront

Saturdays – 10:00 a.m. – 5:00 p.m.

Sundays – 11:00 a.m. – 4:30 p.m.

If Pioneer Square is Portland’s Living Room, Waterfront Park is the Patio. Special events such as Rose Festival, Fourth of July, Pride, the Oregon Brewer’s Festival and more are held here on the edge of the Willamette River. Enter at the Portland, Oregon sign area and this is the spot where Saturday Market is held. The Market currently holds the record for the longest continuously operated open air market in the US. The vendors that are mostly local small businesses sell absolutely anything and everything- crafts, food, clothing, games- you name it. Portland loves shopping local and we love when our tourists shop local too, so this is the ideal place to pick up a souvenir!

10. Mill Ends Park

Maritime Museum hours- Wednesday, Thursday and Friday 11 AM-4 PM

From here continue walking down Waterfront Park Trail, passing the Oregon Maritime Museum on the water. On Taylor Street and Naito Parkway which runs parallel to the Waterfront, you’ll see a conspicuous median. This median actually holds the Guinness record of being the smallest park in the world, apparently built for leprechauns. This is the last stop on my walking tour, but Waterfront Park continues for about three quarters of a mile. Another option for an extended tour and bridge view is to walk across Hawthorne Bridge and continue to the Oregon Museum of Science and Industry.