May has always been a meaningful month in our family. Obviously, Mother’s Day is this month, but for us May is the sweetest because both of my daughters celebrate their birthdays. It’s a month that invites reflection, celebration and a bit of nostalgia as I think about all the moments we’ve shared, many right here in the Portland area, where the girls grew up.
 
Over the years, we’ve created a collection of rituals and favorite spots that have become the backdrop to so many milestones, big and small. So, this May, I am sharing a little roundup of the places and experiences that have brought us joy over the years. 

Dinner at Nostrana

Our absolute favorite restaurant, Nostrana has been the site of more than one celebratory dinner for our family. It’s one of those rare places that manages to feel both special and welcoming whether you’re there as a family, a couple or with a work group. Our family’s go-tos are the Grilled Beef Tagliata (a perfect medium-rare steak with arugula), the wood-fired margherita pizza (plus scissors, of course), the Insalata Nostrana salad (I promise a radicchio Caesar is a thing of beauty), and of course, Pizzeria Mozza’s butterscotch budino for dessert. If you don’t leave absolutely stuffed, you’ve failed the assignment.

Breakfast at Waffle Window

We live south of Portland so venturing to SE Hawthorne on a Saturday morning takes a bit of effort, but boy is it worth it. Sweet, savory, or somewhere in between, there’s something about walking up to that cheerful little window and ordering a liege waffle piled high with goodness that feels like pure Portland magic. We always linger at the sidewalk tables, watching the neighborhood come to life.

Summer Nights with the Portland Pickles

One of our favorite low-key, high-fun family outings is catching a Portland Pickles game at Walker Stadium. We love watching from the picnic tables, snacks and an IPA in hand, soaking up the neighborhood ballpark vibe. The games are goofy, the fans are loyal and there’s just something joyful about a summer evening under the lights.

80s Movie Nights at the Hollywood Theatre

There’s a special kind of bonding that happens when you introduce your kids to the movies you loved at their age. Watching Top Gun at the Hollywood Theatre -surrounded by other people clearly reliving their glory days – was a highlight. There’s something about that old marquee, the vintage seats and the sense of shared nostalgia that makes it more than just a movie night.

Ski Getaways to Cooper Spur

Thanks to Gretchen on our team for introducing me to Cooper Spur. Just a couple of hours from Portland, it was our go-to ski spot when the girls were young. It’s the ideal place to ease into ski season (or shake the rust off), and it has just the right mix of cozy charm and outdoor adventure. The best part is you can rent a room or cabin, enjoy dinner in their lodge and put off the drive home until the next day.

Holiday Traditions at Sleighbells of Sherwood

While May is our season of birthdays and blossoms, the most rooted traditions always seem to fall around the holidays. Every year, the girls and I go to Sleighbells for special annual ornaments, a box of their impossibly good fudge, and of course, a photo with the Big Guy himself. It’s one of those traditions that marks time, year after year, regardless of how old the girls get!

Being a mom and raising my girls has been the highlight of my life.  While one is finishing her first year of college and the second is about to be a junior in high school, they’ll always be my “kids,” and we’ll never stop making new memories, while reliving some of our favorites!

If you’re local, I hope this list gives you a few ideas for memory-making this May. And if you have your own favorite spots or traditions, I’d love to hear about them. Wishing you a joyful month full of connection, celebration and (hopefully) sunshine.