If you like Voodoo Doughnuts

Voodoo Doughnuts has been a tourist trap original Portland doughnut shop for years, and while locals find the doughnut quality debatable, their creativity can’t be denied. Where else can you eat a giant phallic shaped cream filled doughnut named “Cock and Balls” and a doughnut topped with (often stale) Cap’n Crunch cereal? Regardless, I believe they still make decent doughnuts, although not good enough to take a pink box back to the Netherlands like I witnessed on my last flight. Since Voodoo has blown up they are now opening multiple locations in Japan, and have locations in Austin, Denver, Eugene, and Universal Citywalk. You may have to brave hour long lines at the original downtown location, so consider heading a few miles away to the Northeast location or to their food cart at Cartlandia.

Try: Blue Star Donuts

Blue Star opened later than Voodoo, 2012 to be exact, and they were so successful that there are now locations in Southern CA and Japan. They don’t have as wide of a selection as Voodoo but enough to satisfy anyone’s taste buds. They also have a location in Portland International Airport before security. While their slogan is “Donuts for Grownups” the flavors are certainly not boring, with sophisticated sounding flavors like “Blueberry Bourbon Basil” and “Lemon Poppy Buttermilk.” They pride themselves on not having artificial sugars and ingredients and using cage-free eggs (although they have vegan options too) and are prepared fresh daily in the morning.

If you like the Japanese Gardens 

The Portland Japanese Gardens get a lot of crowds and just completed a 33.5 million expansion- which helps justify the $15 for adult admissions. The tranquility and relaxing vibes can be dampened by the hard-to-find parking and crowds so for best results try to avoid weekends, head over around opening time, and during a non-sunny day. Prior to the expansion the Garden even with a slow stroll was completed in about 30 minutes, so if interested try to combine with the free Rose Garden (if in season) which is walking distance or a nice hike at nearby Forest Park.

Try: Crystal Springs Rhododendron Garden

Crystal Springs is an easily miss-able attraction nearby small liberal arts Reed College in the Eastmoreland neighborhood. It’s very underrated compared to the Japanese, Rose, and Chinese gardens that get a majority of the tourists. The park is expansive than the other gardens, and has a large walk-around pond with ducks, small waterfalls, and plenty of rhododendrons and other flowers. A local secret is the free admission on Mondays and Tuesdays, and admission the other days is only $5 with free parking either onsite or at Reed College.

If you like brewery hopping in the Pearl District 

Since a majority of places to stay and historical hotels reside downtown, the Pearl District is a popular area to brewery hop. The breweries have great beer, but are also popular with long wait times and some are not local- Deschutes and 10 Barrel hail from Bend, Fat Heads is from Ohio and Rogue is from Eugene. If you want to stick with Portland breweries Back Pedal and PINTS (in Old Town) are local, but Deschutes (NW style), 10 Barrel (pizza) and Fat Heads (burgers & wings) all make amazing food. Tours include PDX Pedicab, BrewCycle, and Brewvana.

Try: Eastside PDX Ale Trail

Someone finally made a map with close-in East side breweries! Similar in concept to the Bend Ale Trail which I recommend all beer lovers do, all participating breweries have a “passport” that can be stamped. Some ways to explore the trail include  Brewvana Brewery tours,  Pedalounge, PDX Pedicab and of course a self tour can be done walking or biking. There are so many breweries on the list it would be inadvisable to try them at one time. Highlights include Ground Breaker for gluten free beer, Cascade for sour beers, Basecamp and Baerlic have my favorite for beer, and Burnside and Ground Breaker have the best food.

If you like shopping on NW 23rd 

Northwest Portland is full of older Victorian houses that have since turned into spaces for coffee shops, boutique and chain stores, and restaurants in the Nob Hill area. Similar to the sister city in San Francisco it is well connected by public transit and close to many downtown hotels which makes it an ideal place for many out of towners to shop and dine. Since this area is one of the most expensive places to rent in Portland, these shops are more high end boutiques and chain stores, although there are some lower priced places such as their World Market, Sloan Boutique, and Three Monkeys.

Try: Shopping on Hawthorne or Alberta

It’s easy to spend a whole day in the Hawthorne area with movie theaters, bars, Quarterworld, Helium Comedy Club, restaurants, people-watching, and shopping galore. Concepts that can be found only on Hawthorne such as Rachel’s Ginger Beer, Metro Boutique and Naked City Clothing (great place to get costume items!), and the Red Light Clothing Exchange– one of the largest used apparel shops in Portland. There is an extension of Powells Books (a fraction of the size of the downtown location) and The Gold Door, my favorite art, jewelry and gift shop to take guests when they visit.

Alberta Arts District is plenty of fun and can be combined with nearby Mississippi Avenue for a day of exploring Northeast Portland. The last Thursday of the month Alberta hosts a “Last Thursday” street fair and invites any vendor to sell their wares. “Shop Local” is a mantra adopted here, with many inclusive signs dotting storefronts and promotions of local artists and designers. Every Wednesday Alberta has a “Retail Happy Hour” from 3-6 PM offering discounts to shop local. Some highlights include Collage Annex a crafting and hobby store, Local Discoveries a unique NW gift shop and Portland Hemp Works, with all things hemp-related.

If you like Multnomah Falls

Multnomah Falls gets lots of foot traffic- so much so that parking fills up very early especially on sunny days, holidays and weekends. It’s understandable that this is on many first-timers itineraries since it is beautiful, the highest waterfall in Oregon, and less than an hour from most areas of Portland. The hike itself is 2 and a half miles round trip and moderately easy, although people having difficulty hiking can see the falls from the bottom as well. Sometimes the bridge is closed for repairs, which can be a source of frustration for those who have traveled farther to do the hike. Fortunately there are many other waterfalls and hikes to be had in this area just moments away!

Try: the other Columbia Gorge Waterfalls

There are 25+ waterfalls besides Multnomah Falls to explore, the level of hiking difficulty ranges from walking 50 feet from the car to the viewpoint (Horsetail Falls) to climbing over a log jam and wading a mile down a 4 ft freezing river (Oneonta Falls). Midweek prior to 11 AM or during times of less desirable weather are good times to arrive for less crowds although none of these get quite as crowded as Multnomah.

If you like Oregon Brewers Festival

OBF is definitely where the party’s at- Portland’s largest annual beer festival has the most breweries, people, and hours of operation. The downside is the long lines that can leave your beer glass empty more often than not, and beers being tapped out before you’re able to try them. Tables at Waterfront Park get sticky and crowded very quickly, and there is little shade from the hot July sun besides the muggy tent in the middle with the sticky tables. The best times to attend are Wednesday (opening day) and Sunday around opening. Friday afternoons/evenings and all day Saturday is the most claustrophobic.

Try: Organic Beer Festival, Portland Fruit Beer Festival

I have been to more beer and cider festivals than I care to admit, but these two are my favorite and are privy to more locals than out-of-towners. Organic Beer Festival takes place at Overlook Park in North Portland and pour from about 50-60 beer, wine, and mead vendors which is enough to have some variety without an overabundance of choices. There is cornhole, frisbee, and other games going on on the lawn, live music, and enough space to bring lawn chairs and hang out with friends while waiting only a couple minutes at the most for a taster.

The Portland Fruit Beer Festival is good fun, even for those who do not like “fruity” beers. To take part in the FBF, the brewery just has to have real fruit as an ingredient- so there are even stouts, ciders, sours, IPAs, Kolsch, etc. There are about 30 different beers, just enough to try a lot of them! The location is at Burnside Brewery so not a lot of room to sit down and play games but the beers here are for the most part phenomenal and the food at Burnside is outstanding.

If you like Ground Kontrol

Ground Kontrol is a classic Portland arcade bar that opened in 1999, and was the go-to for anyone who wanted a night of fun pinball games with their liquor. It is also open to minors from noon-4:30 PM. It has recently been working on an expansion which is good because it gets extremely sweaty and crowded (especially on weekends or downtown events). Its location in Old town/Chinatown makes it easy choice for a group night-capper after a downtown festival.

Try: Quarterworld

Ground Kontrol held the monopoly of having the most pinball games in the Portland area- and then Quarterworld came around in spring 2016 and took that record away. It occupied the historical former Alhambra Theater on SE Hawthorne and unlike Ground Kontrol lets minors play until 8 PM. They have a back bar with games and a movie theater and a huge open room of every game imaginable- even skeeball for those who aren’t great at pinball. The location on Hawthorne makes it easy to bar hop or grab a bite at one of the awesome nearby restaurants, and Quarterworld allows food to be delivered in. There is a $3 cover charge (Ground Kontrol also has a cover on weekends and events) not including the price of the games or drinks.

If you like restaurants on Division 

SE Division is a bastion of high end restaurants and many that make foodie lists of  of places to go such as Salt and Straw and Pok Pok. Be forewarned that parking is a complete nightmare and there isn’t a direct MAX line connecting downtown to Division, so Uber, Lyft, bike, and bus are the best options. If one must park down there I’d recommend finding a spot and walking in between Hawthorne and Division and making an afternoon of it. The neighborhood is extremely bike friendly as well, so bikers rejoice as long as Division Street itself is avoided- it’s usually a congested mix of construction and people looking for parking. Lists of top Portland restaurants have a few Division restaurants as “must eats” but my wallet and I haven’t understood the hype after eating at some of those places. With that being said there are some awesome food carts there that can satisfy anyone’s palate and Stella’s Tacos is tasty.

Try: Mississippi Ave

North Portland’s Mississippi Ave in the Boise neighborhood is conveniently located off the I-5 and the MAX’s yellow line, and boasts multiple bars, restaurants, and it’s own food cart pod. The area is also featured in more than a few Portlandia episodes due to the eccentric shops such as “Paxton Gate” and the alternative venue Mississippi Studios. Some highlights include brunch at Sweedeedee, a cocktail at the vintage looking Liberty Glass or Bar Bar, German beer bar Prost!, brewery Ecliptic and local icecream favorite Ruby Jewel.