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Top 10 Date Ideas in Portland Oregon (Romantic & Fun)

Portland, Oregon has the reputation of being one of the more quirky and weird cities in the United States. The city of roses is, however, also a wonderful place for couples to have a romantic weekend getaway. From its lush nature to its fascinating architecture and from its beautiful river views to its gorgeous gardens, there is something for every couple to explore and enjoy.

Narrowing it down to 10 ideas was difficult, there are so many things to do in this city and its surrounding areas, whether you’re in the mood for fun or relaxation. We’ve curated the list to include only the must-do activities when visiting the beautiful city of Portland.

1. Explore the Portland Japanese Garden

With its meandering streams, intimate walkways and spectacular view of Mt. Hood, it is no wonder that the former Ambassador of Japan to the United States call the Portland Japanese Garden “the most beautiful and authentic Japanese garden in the world outside of Japan.” There are many styles of gardens showcased in this serene 5.5-acre garden. There is even a waterfall and a teahouse. Located in one of Portland’s most icon areas - Washington Park - the garden overlooks the city and provides an oasis from the city life surrounding and below.

The garden was designed in 1963 with the hope to provide a peaceful setting to escape worldly concerns and an opportunity to get outside oneself. This is a perfect place for couples to come and enjoy together the serenity that can come from a connection to nature and an appreciation of excellent craft.

2. Picnic at Pittock Mansion

View of downtown Portland and Mt. Hood from Pittock Mansion
View of downtown Portland and Mt. Hood from Pittock Mansion

If you love Victorian and French Renaissance architecture, Pittock mansion is the place to visit in Portland. This mansion was built by Henry Pittock, a 19th century newspaper man who turned The Oregonian into a successful daily newspaper that is still printed today. Located in the West Hills near Forest Park, the mansion provides panoramic views of Downtown Portland. Being on the National Register of Historic Places since 1974 means that it has been kept in immaculate shape and the grounds are pristine.

The grounds are an ideal location for a picnic. Bring a blanket and enjoy the beautiful views of Portland, the confluence of the Columbia and Willamette rivers and majestic Mt. Hood. This is one of the most romantic spots for a view that Portland has to offer.

3. Enjoy a romantic cruise on the river

A great way to see much of the downtown area is from the river. Portland sits at the confluence of the Columbia and Willamette rivers. A river tour, whether its at brunch or a sunset dinner cruise, provides an excellent opportunity to enjoy landmarks like the Portland Old Town Sign and Elk Rock Island. On the river is one of the most romantic spots in all of Portland.

If you book a sunset dinner cruise, you’ll be entertained by live music as you enjoy a three-course meal. The champagne brunch cruise, on the other hand, is a two-hour excursion that includes a buffet brunch and champagne.

4. Sail on the Columbia River Gorge at sunset

Another way to enjoy the beautiful views from the river as well as the stunning Columbia River Gorge, is to go sailing at sunset. The Columbia River Gorge offers stunning views of natural scenery with lush forests and steep cliffs as well as charming towns like Hood River. There is really nowhere quite like it in the Western United States. Catching the views of the sunset as well as the starry night sky will provide one of the most romantic dates on this list.

5. Sample local wines in the Willamette Valley

The colors of the Willamette Valley vineyards in the fall
The colors of the Willamette Valley vineyards in the fall

If alcoholic beverages are your thing, then Oregon Wine Country will make for a lovely excursion. With the Willamette Valley Wine Tour, try pinots, chardonnays and rieslings on a 7.5 hour trip with experienced guides. You’ll learn the history of winemaking in this beautiful valley and enjoy the day with other wine connoisseurs. There will be spectacular, romantic views on this full day of wine tasting.

6. Wander through Multnomah Falls and the Columbia River Gorge

For couples who are more the outdoorsy type, there are gorgeous waterfalls to explore in the Portland area. Multnomah Falls, located in the scenic Columbia River Gorge is the most famous. These dazzling 620’ foot falls are surrounded by the lush greenery that is so common in the Pacific Northwest. This narrow waterfall is a great place to launch a hike or simply enjoy a romantic picnic. While you’re in the Columbia River Gorge, enjoy the amazing hikes in the area. Wander through thick forests to crystal clear lakes in one of the most stunning locations in the Portland area.

7. Romantic drive on Sauvie Island

If you’re looking to escape the hustle and bustle of the big city and enjoy quiet, serene landscapes, Sauvie Island is the place for you. An island in the Columbia river, Sauvie is both rural and wild. A spectacular location for birdwatching or even a romantic drive through the countryside, you’ll find charming barns and houses scattered throughout the countryside. Stop along the shore of the river to dip your feet in and skip rocks. If you arrive early in the morning in the fall, there will often be a misty fog that will add to the mystic of this place as well as the romantic vibes.

8. Smell the roses at the International Test Rose Garden

What’s more romantic than roses? It’s for good reason that Portland is known as the City of Roses. When the roses are in bloom, they are magnificent. The best place to see the roses is at the International Test Rose Garden. In close proximity to the Portland Japanese Garden (in fact, it might even make sense to hit them both up in the same outing), this garden features over 650 species of roses and more than 10,000 rose bushes. The fragrances and colors will blow you and your romantic partner away. The best time of year to go to see the roses is in September or early October. The Portland Rose Festival is usually held in early October.

9. Stroll through the Pearl District and along the waterfront

Walk or bike along the Willamette River waterfront
Walk or bike along the Willamette River waterfront

The Pearl District is one of the most iconic in Portland, Oregon. It is also one of the most romantic. A casual stroll through this area and along the waterfront, especially in the evening hours, will be one of the more romantic experiences that Portland has to offer. Enjoy one of the several fine restaurants this neighborhood has to offer. And afterwards, continue your stroll along the waterfront and enjoy the dazzling city lights reflecting off the water.

10. Go to the movies like in the old days

When your eyes need a break from all the lush green scenery in Portland or if you just simply love movies, the Cinemagic Theater is a wonderful place to go see a classic movie together. Everybody knows that classic movies are the most romantic. And the intimate setting of the Cinemagic Theater will set just the right mood for you and your romantic partner.

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