As a boudoir photographer in Portland, Oregon, I’m often asked about fun date ideas they can take their partners after their boudoir session, since they usually leave my studio in full glam hair and makeup, and they might as well take advantage of it!

Since I’ve lived here for about seven years now, I’ve had plenty of time to explore and discover the best spots for a memorable outing. Whether you’re planning a first date or looking to spice up your regular routine, I’ve got you covered with these date ideas in Portland, Oregon that are sure to impress! 😜

Image depicting a woman taking a stroll through the International Rose Test Garden in Washington Park, Portland, Oregon

1. Spend the Day in Washington Park

Washington Park is a true Portland gem, offering a mix of natural beauty and fun activities for the perfect outdoorsy date!

The Tennis Courts: Get Active Together

Challenge your partner to a friendly match at the park’s public tennis courts! It’s a great way to get moving and enjoy some fresh air together.

Image depicting young couple high-fiving on a tennis court — Photo by Erwans Socks

The Rose Garden: A Romantic Stroll

After working up a sweat, you could take a stroll through the International Rose Test Garden, where over 10,000 rose bushes bloom. It’s a romantic spot with stunning views of downtown Portland and Mount Hood. Find a quiet bench to enjoy the fragrance and take in the beautiful scenery.

Rose bush growing orange flowers — Photo by Irina Iriser

The Archery Range: Hit the Bullseye

Image depicting two archery targets with an arrow sticking out of the center of one — Image by Mikhail Nilov

For something unique, visit Washington Park’s archery range. Bring your own equipment and test your skills in a peaceful setting. If you’re a beginner, maybe sign up for some archery lessons before attempting this on your own! Whether you’re experienced or a beginner, it’s a fun way to spend time together and maybe learn something new!

Have a Picnic!

After your activities, unwind at one of the many picnic tables scattered throughout the park, or bring your blanket and set up on the grass! Pack a basket with your favorite snacks and enjoy a meal surrounded by lush greenery. It’s the perfect way to end a day at Washington Park.

2. Explore the Portland Japanese Garden

Right next to Washington Park, you’ll find the Portland Japanese Garden—a peaceful escape from the city’s hustle. Wander through the meticulously designed landscapes, enjoy the koi pond, and take in the stunning views of Mount Hood. It’s a tranquil spot that’s perfect for deep conversations and quiet moments together. Make sure to check out their event schedule to see if you can catch something memorable!

Japanese style architecture of circular window with Japanese foliage outside — Image by Ryutaro Tsukata

3. Wine Tasting Experience

Portland isn’t just close to wine country; the city itself offers some fantastic wine tasting experiences. Here are a couple places where you can enjoy a glass (or two) without leaving the city!

Coopers Hall

Anonymous woman drinking a glass of rose wine in tasting bar — Image by Elina Sazonova

Coopers Hall is a winery, taproom, and event space all rolled into one. Situated in a renovated warehouse in the Central Eastside, it’s known for its sustainable practices, including wine on tap. The spacious, industrial-chic setting is great for both casual sipping and more formal tastings. Pair your wine with delicious, locally-sourced food from their menu.

Division Wine Co.

Part of the SE Wine Collective, Division Wine Co. focuses on creating French-inspired wines with a Pacific Northwest twist. Their urban winery is a great place to explore unique varietals and blends that you won’t find anywhere else. The tasting room is inviting and staffed by knowledgeable guides who can walk you through the tasting experience.

4. Kayak or Paddle board the Willamette

If you’re looking for a bit of adventure, rent a kayak or paddle board and check out a bit of a different view of the city from the Willamette River. You’ll get a unique perspective of Portland’s skyline while enjoying the peacefulness of being on the water. For an extra romantic touch, go at sunset when the city is bathed in golden light.

Image depicting two people paddle boarding on the Willamette River in Portland Oregon — Courtesy of Gorge Performance

5. Relax at McMenamins Kennedy School

For a date that’s a bit out of the ordinary, check out McMenamins Kennedy School. This historic schoolhouse has been converted into a hotel with a brewery, soaking pool, movie theater, and more! You can grab a drink, see a movie, or even stay overnight in one of their unique rooms. It’s a fun and quirky spot that’s quintessentially Portland.

People relaxing in the soaking pool at Portland Kennedy School — Credit: Ashley Anderson

6. Thrift Shopping on Hawthorne

If you're looking to go thrifting in Portland's Hawthorne neighborhood, here are three must-visit stores:

House of Vintage

A massive thrift store with over 60 vendors offering a wide variety of vintage clothing, accessories, and home decor. It’s a treasure trove for anyone looking for unique, retro finds.

Crossroads Trading Co.

This store offers a curated selection of gently-used, trendy clothing and accessories. It’s a great place to find name-brand items at a fraction of the cost.

Red Light Clothing Exchange

Known for its eclectic mix of vintage and contemporary secondhand clothing, Red Light Clothing Exchange is a well-organized store with a diverse selection of styles and accessories.

Whether you're exploring the lush beauty of Washington Park, sipping wine in one of Portland’s urban wineries, or hunting for vintage treasures in the Hawthorne neighborhood, these date ideas in Portland, Oregon offer something for most everyone. The city is full of unique experiences that can turn an ordinary day into a memorable adventure with your partner! Happy dating 🥰

Want more tips on creating unforgettable experiences? Join my Facebook group, Foxfire Vixen Society, to connect with other amazing women who love exploring Portland as much as you do. Can’t wait to see you there!

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