Seen through the eyes of Regina Leonard

Who went: Jeannine Kahn, Regina Leonard, Mia Smith and Terrel Thomas

We went because: Since 2008 our group has traveled every fall to run a marathon at an interesting destination. This year we selected the Portland Marathon because Runner’s World named it “the best people’s marathon in the West.”

Hotel recommendations: We stayed at the Portland Marriott Downtown Waterfront, which has great views of the Willamette River. Staying downtown puts you in the heart of Portland, within walking distance to many city attractions, restaurants and shopping.

Where to eat: We got a great sampling of locally brewed beers at The Rock Bottom Brewery. (Portland, and the entire state of Oregon, is known for its microbreweries.) Dinner at Mama Mia Trattoria was like taking a step back in time into a traditional Italian restaurant; the food was delicious. And of course, we couldn’t pass up sampling the famous Voodoo Doughnuts while in town! We highly recommend the Captain My Crunch doughnut.

Favorite dish on the menu: At Mama Mia Trattoria, we ordered spaghetti and meatballs, lasagna and veal parmesan. Everything is made from scratch, and Grandma Mary’s Sunday Gravy was well worth the trip. So is the bread!

Items of clothing you shouldn’t leave home without: For this trip, our running shoes were imperative. We did trade them in for cute flats and boots for our wine-tasting excursion.

Local attraction worth a drive-by: The day after the marathon, we took a 30-minute drive to Willamette Valley, home to some amazing wineries. Our tour was with WineDirt; our tour guide, Mary, took us to five wineries for tastings and conducted a fun yet informative wine class.

A great experience off the beaten path: The Four Graces Winery. Owned by the Black family, the 20-acre estate is a sustainable farm that produces Pinot Noir, Pinot Gris and Pinot Blanc wines. We enjoyed a private tasting of its best wines, strolled through the demonstration vineyard, ate a picnic lunch in their historic farmhouse—and each left with a bottle of wine.

Worth the splurge: Taking a guided wine tour with a driver and a professional oenologist is worth every penny. Our guide was local, knew all the boutique wineries, and had a vast knowledge about the world of wine. She planned a day for us that exceeded our expectations.

Something surprising we learned on the trip: We all now love Oregon Pinots. As for running, we found out that Portland has some killer hills, especially when you are used to running at sea level on flat terrain.

Insiders’ tips: Plan to dress in layers while in Portland. The weather can change quickly.