Lake Oswego is where Madi grew up and has a cute downtown right on the Lake. We recommend Lake View Taphouse, Five Spice Seafood, Mann's On The Lake (great lake views), Baird's On B, Nicoletta's Table, and Salt & Straw for a scoop of ice cream. There is a great farmers market on Saturday mornings as well.
For those of you interested in exploring Portland, we recommend the Northwest and Hawthorne neighborhoods. The Portland Japanese Gardens are beautiful as well.
If you plan on renting a car, we highly recommend exploring the Willamette Valley as it is home to some of the best Pinot Noir in the country. We recommend Domaine Serene and Stoller Family Estate wineries in Dayton, OR.
The Columbia River Gorge is an absolutely stunning place with views of Oregon and Washington. It is stocked full of hikes of varying difficulties and great restaurants. If you have never been to Oregon before, Multnomah Falls is a must-see. We also love the Angels Rest hike for a bit more of a challenge. Hood River is a great spot to grab lunch as well. (About 45 minutes away)
Mount Hood is a beautiful spot in the summer & winter. One of our favorite hiking trails is Tom, Dick & Harry mountain. Timberline lodge is pretty spectacular as well. (About 1 hour away)
The entire Oregon coast is absolutely stunning and very different than any other beach in the country. Cannon Beach is a place where Madi's family has gone every summer since she and Chris started dating and is the spot the Willihnganz's get to share with the Young's the weekend before the wedding. (About 2 hours away)
Mount Rainer National Park is about a 2-hour drive from the Portland area. We highly recommend the Skyline Loop trail.
For those of you staying in Oregon for a few extra days, we definitely recommend checking out Bend, Oregon (3 hours away). It is one of our favorite cities filled with a lot of hiking, biking, and breweries. Crater Lake National Park isn't too far from there either.
If you're planning on renting a car and staying a few extra days, why not check out Seattle (about a 3 hour drive from Portland area) - Madi and Chris love the National Parks around the area as well as the many fun spots right in the city such as rooftop bars with views of the Space Needle, Pikes Place Market (watch out for the flying fish!), Discovery Park, and of course, the FIRST Starbucks (a must for Madi)!