24 hours in Hillsboro, Oregon: Wine, dine, and play all day

As the weather starts to turn warmer and sunnier, it’s worth taking a day to enjoy the beautiful PNW spring. But what’s there to do in Hillsboro, Oregon?

The answer is: SO MUCH! Whether you’re in town for the first time or you’re a local looking for a few new things to do, we’ve planned a perfect day that will take you through some of Hillsboro’s most beloved spots, from morning to night. 

Keep reading for your itinerary, and get to know our city a little better. 

Morning: Window shop on Main Street

Downtown Hillsboro is full of hidden treasures waiting to be discovered, making it the perfect kickoff point for your adventure. Start your day with a stop at Insomnia Coffee, where you can enjoy a warm beverage and a delicious pastry. Soon to open a brand-new location in Reed’s Crossing Town Center, Insomnia offers a relaxed and inviting atmosphere—a fantastic way to set the tone for the day ahead. 

Once you’re caffeinated, wander the neighborhood and take in the cozy small-town vibes. Browse unique home décor at Belladonna or White Birch Design Company (also opening soon at Reed’s Crossing Town Center), or get lost in the treasure trove that is Le’Stuff Antique Mall. Foodies might want to stock up on artisanal goods at Bennett Urban Farm Store. Book lovers may find the next title to add to their TBR pile at Arcade Book Exchange. Finally, pop into popular bakery Decadent Creations to pick up some treats to nibble throughout the day.

Early afternoon: Explore wine country

Home to two-thirds of Oregon’s wineries and vineyards, Willamette Valley is known as one of the premier pinot noir–producing areas in the world. It’s also an ideal day trip destination! About 15 miles from Reed’s Crossing, nestled in the Willamette Valley within the Chehalem Mountains, you’ll find a number of esteemed wineries such as Ardiri Winery & Vineyards, CHO Wines, Beaux Frères, Colene Clemens, Eminent Domaine, Fairsing Vineyard, Jachter Family Wines, Sequitur, and Six Peaks Winery. 

Imagine a sunny drive through rolling hills draped in lush vineyards, the landscape a patchwork of verdant vines and distant mountain peaks. You might take a guided tour to learn about the winemaking process from grape to glass, savor your sips alongside a charcuterie board, or wander through the vines, snapping photos of the picturesque scenery. Once you’ve sampled a few delicious options, you’ll be ready to continue your day at our next stop. 

Late afternoon: Commune with nature 

Boasting 35 public parks that offer diverse recreational opportunities, Hillsboro is an outdoor lover’s dream. From expansive spaces like Rood Bridge Park to the seven unique parks located within Reed’s Crossing, there's an impressive variety of environments and options for such a small city.

For those who love glimpsing local wildlife, Hillsboro is also home to several protected natural areas. A visit to Jackson Bottom Wetlands Preserve offers a tranquil escape where you can view diverse birdlife and explore peaceful trails amidst a restored wetland habitat. Orenco Woods Nature Park provides a woodland experience, perfect for a leisurely hike to discover the quiet beauty of Oregon forests. And the Reed's Crossing Greenway invites you to explore its interconnected pathways and greenspaces, home to varied animals including ducks, blue herons, egrets, and even a frog choir that sings out once the sun dips below the horizon.

Evening: Fill your belly at an Oregon institution

Finish your day at McMenamins Cornelius Pass Roadhouse, a tree-filled oasis nestled on six acres of former pioneer farm country. The property’s historic charm is undeniable, with the original farmhouse and outbuildings dating back to the mid-1850s when the Imbrie family first settled the land.

If you’re in the mood for a nightcap after dinner, explore one of the cozy hideaways on the property. The warmth of the wood stove in the Little White Shed is especially inviting on a cool evening—perfect if you enjoy a whiskey drink. If that’s too crowded, the Redwood Room is another spot to enjoy a quiet beverage among the trees. Whether you’re craving comfort food or a craft brew, this historic locale is a wonderful place to end your 24-hour Hillsboro adventure.

A day to remember

From supporting small businesses to a cozy roadhouse hideaway, we’ve provided everything you need for an unforgettable day in Hillsboro, Oregon. So lace up those walking shoes and discover the hidden gems that make this corner of the Willamette Valley a perfect destination—whether you’re taking a trip or looking for a spot to call home.

Still have questions about life in Hillsboro? Take a virtual tour, come by for a visit, or sneak a peek at what’s in store for the future.