4237 N Mississippi Ave, Portland, OR 97217

Summer is the best time to explore Portland’s food cart abundance. Grab a group of friends and hit up the Prost Marketplace food carts at Mississippi and Skidmore for a dinner that fits everyone’s dietary needs, and budgets. Prost is one of the OG food cart pods in Portland. It also has a covered patiO, so you can hang out a bit after feasting. After dinner, walk the few short blocks down Skidmore to Mock’s Crest Park (a.k.a. The Skidmore Bluffs) to experience one of the best views of downtown and a picture worthy Portland sunset.

When to go: 

An hour or two before sunset so you have time to catch up with friends and grab a prime sunset spot at Mock’s Crest.

Pro tip: 

Try having each person in your group order from a different cart for an impromptu potluck. Where else can you have BBQ and sushi burritos, then wash it down with a pint of German beer?

5736 NE 33rd Ave, Portland, OR 97211

The Kennedy School is a former elementary school built in 1915 that McMenamins re-imagined as a Portland hub. Classrooms were traded for hotel rooms, the auditorium is now a movie theatre, and the school has several bars and communal spaces. One of its most iconic features is a Roman-style soaking pool in the courtyard (formerly the teacher’s lounge). The warm, saltwater pool is surrounded by gardens, making it a low-key spot to soak your stress away.

When to go: 

After 6pm, the pool is 18 and over. Time it right and you can catch a movie or a show before you get your soak on.

Pro tip: 

If you live in the neighborhood, you can soak for free!

SE 26th Ave & Stark St, Portland, OR 97214

Want to take a walk through Portland history? The Lone Fir Cemetery in SE Portland has been around since the mid-1800s, and over 25,000 Portlanders are buried here. More than just a cemetery, it’s also the second largest arboretum in Oregon. The cemetery is expansive and you’ll discover something different about it every time you visit. You can easily spend hours winding down the paths and marveling at the moss covered headstones and over 700 different types of trees. It’s easy to see why the Lone Fir Cemetery is one of Oregon’s most-loved historic sites.

When to go: 

Any time of day is great for a shady stroll, but visiting right as it’s starting to get dark adds a spooky vibe to this historic cemetery.

Pro tip: 

Read the headstones and try to find the oldest one or the ones with the most unique inscriptions.

Eastbank Esplanade

Just south of Hawthorne Bridge, the Holman Dock (a.k.a. the Hawthorne Dock) is Portland’s favorite spot to cool off on the Willamette River. The Dock is public and free, making it ideal for laying out and enjoying the water. You can acccess it from the Eastbank Esplanade and there’s ample parking...although we highly recommend going by bike.

The Willamette is familiar to Portlanders as the divider between east and west, but the Dock lets you experience the beauty of the river for yourself. It’s safe and legal to go for a swim, so bring your swimsuit and floaties.

When to go: 

Head to the Dock in the morning if you’re looking for the more exercise-driven crowd. If you’re feeling casual hangs by the water, later in the day is your sweet spot.

Pro tip: 

There’s no shade at the dock, so bring sunscreen and your favorite sunnies to stay cool.

1512 SE 7th Ave, Portland, OR 97214

Distillery Row is the birthplace of Portland’s craft spirits scene. Eastside Distilling’s tasting room on SE 7th is one of the original spots on Distillery Row. Ordering a tasting flight is the perfect way to expand your palate and try different varieties of spirits. Whether you prefer whiskey, vodka, or rum, there’s a spirit to suit your taste. Tasting with a group of friends is an affordable way to spend your afternoon and is cheaper than going to a traditional bar and ordering multiple drinks. Like what you taste? Pick up a bottle or two of your favorite spirits, and a 4-pack of the Portland Mule to keep in your fridge. You’ll be glad you did when the weekend rolls around.

When to go:

When it’s not quite happy hour yet but you’re ready to start drinking.

Pro tip: 

After your tasting, pick up a Distillery Row Passport, and check out all the craft spirits Portland has to offer.

7805 SE Oaks Park Way, Portland, OR 97202

The rink at Oaks Park is every roller rink your friends had birthday parties at when you were a kid. It’s old school in the best way (literally, it’s the oldest roller rink in the country!!), with a classic Friday night vibe and the last Wurlitzer pipe organ in Portland. You can skate with friends in the afternoons during open skate, or roll through a nighttime session like Adult Rhythm Skate (18+) or Gay Skate. Roller skating is an affordable way to tap into your childhood nostalgia and jam to your favorite throwback songs.

When to go: 

When you’re done binging Stranger Things and want to live your 80s dreams. Or plan for Thursdays and Sundays when they play the Wurlitzer!

Pro tip: 

Oaks Park is also a functioning amusement park, so make it a day trip. Start with some rides and end the day jamming out at the rink.

3303 SW Bond Ave, Portland, OR 97239

One of the best views of Portland is from the Portland Tram, an aerial tram that runs from the Marquam Hill neighborhood to OHSU. The tram is one of the most unique parts of Portland public transit and is one of the only aerial trams in the country. Where else can you watch the sunset while riding an aerial car over foresty neighborhoods looking out over the whole city? There are two cars, named after Jean (OSU’s first female engineering graduate) and Walt (OHSU’s first African American graduate) and they leave every 5 minutes, so you don’t have to worry about missing out. The tram is the perfect way to see Portland from a new perspective and bring out your inner kid.

When to go: 

At sunset on a weeknight (the tram runs until 9:30) for Portland’s only aerial sunset view.

Pro tip: 

Check out the lower terminal on SW Moody and Gibbs to see one of the country’s most diverse transportation hubs. There’s also a free bike valet so you don’t have to worry about keeping up with your wheels.

Southwest Hillside

One of Portland’s most unique features isn’t found on any of the typical maps of the city. Just past downtown, there’s a winding series of staircases nestled into the hills of SW. The mostly concrete staircases are integrated  seamlessly into the hillside and appear to lead some place magical. Want to get in your steps for the day? Try walking the 1,188 steps on the stretch of Southwest from I-5 to West Burnside. You’ll get breathtaking views of downtown while winding between trees and historic homes. Check out publicstairs.com to map out your treks, and discover the many treasured public staircases around the world!

When to go:

On a clear day so you can see from downtown to Mt. Hood.

Pro tip:

Want a real endurance challenge? Try doing a trail at Washington Park or Forest Park in between staircases for a workout with a view.

1831 SW Pedestrian Trail, Portland, OR 97201

Every Saturday the PSU campus hosts its farmers market, which is Portland’s biggest weekly open air market. Looking for motivation to get out of bed on a Saturday morning? Start off with coffee and a pastry, then wind your way through the vendors to see what the market has to offer. Load up your bags with fresh fruits, veggies, bread, cheese, flowers, and more. Local musicians provide your Saturday soundtrack and chefs hold demonstrations to take your cooking skills to the next level. The PSU market is the best way to get Portland’s freshest produce and meet the people who make your favorite dishes possible.

When to go: 

Beat the crowds and get first dibs at the best selection from vendors by getting there right when the market opens at 8:30am.

Pro tips: 

Bring your own bag. Leave the pets at home. And, if you get more than you want to carry around the market, drop off your spoils at the info booth’s Veggie Valet and pick them up on your way out.

98 SW Naito Pkwy, Portland, OR 97204

One of the most scenic spots for biking in Portland is Tom McCall Waterfront Park. The park, which used to be a freeway, is a 1.5 mile green belt that winds along the west side of the Willamette River. In 1974 the city decided to ditch the smog and reclaim the waterfront for beauty and bicyclists. If you really want to maximize your chill, rent a tandem bike and let a friend do the leg work for you. The waterfront park is an easy ride perfect for a sunny afternoon of pedaling and exploring.

When to go:

Weekday afternoons are the least crowded, but the waterfront has plenty of fun events on nights and weekends for you to check out after your ride.

Pro tip:

Renting a bike for the day is the best deal per hour, so make a day of it and take your time exploring the waterfront. While you’re riding you may even see the bridges raised for boats going down the river.

1430 NW 23rd Ave, Portland, OR 97210

The best boutique shopping in Portland is found on NW 23rd. You can find some of your favorite specialty retailers all within a few blocks of each other. Outfit yourself for a hike, pick up some new accessories for your pet, have great food and wait in line for ice cream, and now treat yourself to a flight of spirits. In the past couple years, The NW 23rd area has risen up as the unofficial second Distillery Row of Portland, and Eastside Distilling’s new tasting lounge is the perfect spot to try a sampling of your favorite spirits. On your way out of the tasting lounge, pick up a 4-pack of the Portland Mule to keep yourself cool as your adventures continue.

When to go: 

Weekday afternoons might be good for a quieter tasting, but we recommend coming in when it’s busy on the weekend! It’s fun to take your time with your flight, and do some people watching from the lounge.

Pro tip: 

Get the best deal on spirit sampling by trying a flight of spirits at Eastside’s Tasting Lounge. If you and a friend each get a flight of different spirits, you can taste more and be on your way to finding your favorite craft spirit.

Lower Macleay Trail, Start from NW Upshur St. 

One of Forest Park’s most iconic trails is the Lower Macleay Trail, featuring a gentle creek and terrain that’s friendly for multiple fitness levels. If you’re feeling sporty, try running the trail for a scenic workout. For casual hikers, the shady trail with its meandering pathways is a perfect way to spend time exploring Forest Park. The best treasure of the trail is where it meets the Wildwood Trail deep in the woods at the witch’s house. No witches actually ever lived in this stone abode, but the structure has a perfectly spooky vibe that draws you in. This fairytale-like gem is the perfect spot to rest from your hike and soak up the beauty of the park.

When to go: 

Mornings on the trail unlock the magical qualities of the park as the day begins. Enjoy the forest coming to life as the sun filters in between the trees and the fog lifts from the ferns.

Pro tip: 

Don’t rush the trail; take a picnic and enjoy a moment of calm amidst your Forest Park journey.