If you don't mind facing fog or little drizzle, grab a raincoat and walk along Leif Erickson Road. This valleyed, scenic road runs right through the heart of Forest Park and is semi-paved so that your shoes don't get too muddy. A more detailed trail guide is inside this post.
If you're really bored and itching to escape the rain, nothing beats the Oregon coast. The stretch of coast nearest to Portland has a lot to see and do, with an overnight stay in Newport recommended for everyone's sanity.
There are very few places in Portland that my parents can recall by name, but the Kennedy School is one of them. Start this day off right with giant plate of seafood on the river at Salty's, followed by a movie and beers at the Kennedy School. Here's your map.
If you're sick of being in town and want to do something different, head east on I-84 to the Bonneville Dam to witness the awesome spectacle of electricity being generated by water, then hop over the Bridge of the Gods to Bonneville Resort, which has pools and tubs filled with natural mineral water. You'll leave feeling terrific!
This is a very touristy but memorable day that includes a sightseeing cruise of Portland, shopping downtown, a cocktail 30 stories high at Portland City Grill, then dinner at Jake's. It's a great way to show off our bustling downtown while also fulfilling the number one request of most people visiting Portland: to eat seafood.
Located out in Milwaukie by Dave's Killer Bread, Bob's Red Mill has top-notch soup and hot sandwiches, extensive shopping, and a large bulk food section. It's a great place to stop on your way out of town, especially if you are hungry. Note: they are closed on Sundays. Here's your map.
Work up an appetite by touring and tasting at three Portland distilleries, then end the day with a quick jump across the Hawethorne Bridge to Veritable Quandary. This charming restaurant has a private wine room where you can dine away from the noise of the restaurant, which is especially great if your parents are hard-of-hearing.
Multnomah Village is an adorable neighborhood that is filled with good-looking, friendly yuppies and their well-dressed babies. It's a bit south of town, but worth the trip to eat breakfast at Marco's Cafe, go wine shopping at John's market, and window shop as you stroll through the quaint downtown. Here's your map.
NW 23rd has something for everyone: coffee, snacks, fancy grocery shopping, boutiques for the ladies, and girl watching for the guys. Walking this famous Portland street is a great rainy day activity that only takes an hour or two. This 18-block walk starts with the best breakfast in town and ends with you getting steaks for dinner at Zupan's.
Do your parents like to walk and/or you enjoy tiring them out? Great! They'll love this beautiful tour of the Portland waterfront that ends with a hot cup of tea in the unforgettable Lan Su Chinese Garden. Here's your map.
Have a memorable breakfast in McMinnville, stand in awe of the Spruce Goose, then wind your way back to Portland as you stop at world-class wineries along the way. The scenery is breathtaking even in the wintertime and your day ends with everyone having a fun little buzz.
No trip to Portland would be complete without a trip to Powell's City of Books. This daytime outing starts at Powell's, recharges your battery with liquid chocolate shots at Cacao, delights the senses at Cargo in the Pearl, and ends with a square meal and a beer at Deschutes. These places are within four blocks of each other and can be walked to.
Located downtown near snazzy places such Higgins and the Arlene Schnizter Concert Hall, this impressive museum is a great way to tickle your dad's love of history while also showcasing some fascinating features of modern Oregon. The Oregon Historical Society has rotating exhibits and costs $11.00 for admission.
Grab an umbrella and a smartphone with Google Maps for this trifecta of high brow activities that your parents will love. The day starts with a tour of Pittock Mansion, a downhill stroll through the upscale houses of the West Hills, and ends with a well-earned lunch or dessert at Papa Hyden's on NW 23rd. It's a parent's perfect afternoon!
Portland day trip takes you west on I-84 to Multnomah Falls, then
leisurely backtracks to the Vista House at Crown Point and to
McMenamin's Edgefield for lunch. Extra time even allows for a little
tax-free spending at the Columbia Gorge Outlets. Here is your map.
Are your parents religious? Get them to the Grotto right away! The Grotto offers 62-acres of impeccably maintained gardens and walking paths, studded with chapels, over 100 religious statues and shrines, and reflection spaces. Yes, it's very Catholic-focused, but the Grotto is one of Portland's largest green spaces and best kept secrets, plus you get to take an elevator ride up an 110 foot cliff. Here's your map.
You know what's fun to do in the rain? Drive around and look at stuff from the comfort of your car. This sweet little day trip takes you across the stunning St. John's Bridge to Sauvie Island, where you can drive around admiring the countryside, bird watch, look at cute house boats, or see the sandy banks of the Willamette River.
If you have the time and money, plan an afternoon of wine tasting followed by a a night in Hood River. Located just 60 miles west of Portland, Hood River offers a small-town vibe crossed with "this is what it must feel like to be a rich person on vacation in Aspen" feeling. The downtown is adorable and filled with boutiques and quaint restaurants. Full Sail Brewery is also located here and a fun place to visit.
Safeway and Fred Meyer's have sales on Alaskan King Crab and local crab frequently during the winter. If your parents are not from the NW, they'll flip out for crab legs that cost $35 a plate at a restaurant back home. The crab legs come pre-cooked when you buy them in the store, but serving them at home is an adventure in itself and eating them is silly, messy fun.
Fine dining and fine art: it's a one-two punch that would impress anyone visiting Portland, parents included. Obviously this perfect night is a matter of timing, so plan ahead by making a dinner reservation at Park Kitchen for the first Thursday of the month.
If you have a dog and enjoy walking, bundle up and head out to the 1000 Acre Dog Park in Troutdale. This enormous canine playground is entirely off-leash and filled with happy dogs and people, especially on the weekend.
Sure, it's more fun to go here with your stoner friends, but OMSI is a wonderful museum and a great place to wander around for a few hours during the day. OMSI offers a unique feature: you can still be with your parents here but not having to entertain them the whole time. Instead, everyone can drift off and get lost in their own thoughts or listen to audio guides via headphones.
The first time my midwest parents came to visit me in Portland during the winter, we spent a lot of time indoors just staring at each other. Bars, bowling, and live music were not an option, so it got me to thinking: what do people do in Portland when it rains? I started keeping this list.
My brother also took my parents to the Florida Room on Killingsworth to get a drink once, and I've been trying to correct my parents' tarnished image of Portland ever since. Seriously, who takes their conservative Republican parents to the Florida Room? From that moment on, I decided my parents would only see the natural beauty, ritzy neighborhoods, amazing restaurants, and unique culture that lured their kids out here in the first place.
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