*Highly recommend. Portland is in a rain forest, but September is an optimal time visit and experience the beautiful environment while it is dry and sunny. Lower Macleay is a great entry-level hike where people of all ages and experience levels can experience an excellent bio-diverse slice of Oregon free of charge. With the trailhead located in the city, it's easily accessible, and you can choose the length of your adventure. If you hike to the top (45 min) at Pittock Mansion, you'll get a fantastic overlook of the city. From there you can hike back down, or grab a rideshare if you want to move on to your next adventure :)
*Highly Recommend If you have car access, take the very scenic drive out an hour east of the airport through the The Columbia River Gorge. Lewis + Clark journeyed down the Columbia River and were awestruck (as you will be) by the beauty. Akin to the Grand Canyon, but with a rainforest, there are a multitude of places to visit, hike, enjoy. If you are just driving, we would recommend you stop at the Vista House at Crown Point, which overlooks the gorge from the top. Multnomah Falls is beautiful too (if you can find parking), but you can drive by and appreciate as well. For more seasoned hikers we would recommend The Eagle Creek or Angel's Rest trailheads.
*Highly Recommend Adorned as 'the best Japanese Garden outside of Japan', this place is truly spectacular. Featuring koi ponds, bonsai, and zen gardens, this tranquil space was meticulously planned and rebuilt in 2017 by master world-reknown Japanese architect Kengo Kuma. Admission is $25 for adults, but well worth the price.
This easy bike loop is a great way to get outside and get to see the city from the waterfont. Rent bikes at reasonble cost through the Nike Biketown app (plugs in with Lyft) or use the Lime app and hop on a scooter. The loop can be completed in an hour, but if you want a shorter version, cross over the Williamette river on the Tilikum Bridge at the southern edge of the loop.
If you are like Kevin and never had good ramen before, let Afuri change your mind. We recommend the spicy tonkatsu (it's not that spicy). The Southeast 7th Ave location is the original location, and boasts beautiful interior design in an old repurposed industrial warehouse, but there is a location in Beaverton as well.
Our favorite restaurant. True Italian, and in true Italian fashion, it can be hard to get a table as their hours aren't always exactly as they claim- so call ahead! Your best bet outside of calling is to stop by and put your name down, then walk nextdoor and enjoy a drink or glass of wine at Piazza Italia-owned Bar Rione. Any and all dishes are excellent, but if we had to pick one it would be the penne arrabbiata (it takes them a whole week to prepare). Ordering a floater dish to share with your table is another good move.
You can't really miss when it comes to food in Portland. Outside of the recommendations above, here are some other spots we really like: Food Cart Pods (there are many, all good), Taqueria El Paisano (tacos/late night, Canyon Rd), Stepping Stone Cafe (breakfast), Boxer Ramen, Han Oak (Korean), Grassa (Italian), Skyline Cafe (old time burgers + shakes), Hot Lips (pizza), Eem (Thai), Happy Lamb Hot Pot, Pholandia (Vietnamese), Kkoki Korean BBQ.
Much like the food in Portland, there are countless bars (which also serve great food) where you can't go wrong. Here's a list of some of our favorites. Prost! (German, food carts nearby), 10 Barrel (Flanders St., innercity rooftop bar), Blue Moon (sports/dive, many bars and food options nearby), Paymaster (pool and dive bar), Revolution Hall (old school turned rooftop bar), Bagdad Theater & Pub (theater turned bar), Mississippi Bar Bar, Victoria Bar, Pope House (bourbon), Great Notion (Alberta, great deck), Departure (innercity rooftop), Rontoms (dive, dance), Digapony (dive, dance), Church Bar (old church turned bar), Mulnomah Whiskey Library (high end whiskey/bourbon). If you want to bar/food hop (walking distance), the 4 areas of the city where some of the above are listed are Mississippi Ave, Division St, SE Belmont St, and 23rd Avenue.