The Most Romantic Valentine’s Day Hikes You’ll Find in Oregon

Look back on how you met your partner. Was it on the bus, lodged in traffic? A buzzing college campus? A friend's hazy party? A lucky swipe on an app? Now, remember your first date. Movies, bowling, and a dinner — if you were sure you could hold a conversation. Then, there's the ultimate Pacific Northwest date: the hike. These plans generally come together after a connection is established. After all, you'll want to feel confident that even with sweat dripping into your eyeballs, this person still finds you adorable.

Whether you're planning a Valentine's Day outing or looking to recapture the magic of your early days together, Oregon is brimming with incredible hikes for you and someone special. All you have to bring is your sense of adventure and your hiking boots!

1. McCall Point Trail, The Dalles

Boasting epic views of the Columbia River Gorge and swathes of wildflowers in the spring and summer, McCall Point should be at the top of your list for a romantic rendezvous outside. With almost five miles of trail and more than 1,300 feet of elevation gain, McCall Point offers stunning views for you and your boo.

2. Lower Cascade Head Trail, Otis

If you've got the moxie, few vistas in Oregon could match the one you'll earn for braving the 1,200-foot elevation gain of Lower Cascade Head Trail. Boasting breathtaking views of the Salmon River estuary and the rugged Pacific, this trek embodies the best of Oregon's coast. Bring your binoculars to spot the wildlife and seabirds that make Cascade Head Preserve their home.

3. Tamanawas Falls Trail, Parkdale

Oregon is known for its jaw-dropping waterfalls. But only one served as the backdrop for a friend's proposal: Tamanawas Falls in Mount Hood National Forest. So, naturally, I'm biased. Meaning friendly or guardian spirit in the Chinook language, Tamanawas is a truly special place. Though the hike is under four miles, it winds through some of the state's most stunning woodland. Like many of our region's most beloved trails, I prefer hiking here in winter. You'll find it's the perfect spot to picnic, surrounded by the lilt of birdsong and the rustle of snow in the trees.

4. Pittock Mansion, Portland

Not every romantic outing needs to whisk you into the wilderness. If you'd prefer an urban hike, few expeditions beat Portland's trail to Pittock Mansion, one of the city's most treasured historic places and a site of romance in its own right. Constructed in 1914 by Henry Pittock for his wife, Georgiana Burton Pittock, the Pittock Mansion was imagined as a place where Georgiana could express her love of gardening and roses. She did just that, eventually becoming a lead organizer of Portland's first Rose Show in 1889. Today, the property also offers visitors one of the most incredible views of the city, best enjoyed at sunset, hand-in-hand with someone special.

Wherever you're located and whatever your experience level, Oregon boasts countless outdoor outings to experience with someone special this Valentine's Day. It's not too late to plan an adventure that neither of you will forget! And if you're looking for even more ways to sweeten up this romantic holiday, be sure to check out our itinerary planner for nearby recommendations!