Wine Tasting in the Willamette Valley

Spend an afternoon sipping on delicious wines in the beautiful Willamette Valley. Oregon City is just a short drive away from some of the best wineries in the region, where you can sample a variety of locally produced wines. Enjoy a leisurely day of wine tasting and take in the stunning views of the valley.

Alternative options: Oswego Hills Vineyard & Winery, Villa Catalana Cellars, Campbell Lane Winery

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Dinner at a Fine Dining Restaurant

Treat yourselves to a delicious meal at one of Oregon City’s finest dining establishments. Enjoy a romantic dinner with your partner in a cozy and intimate setting, where you can savor gourmet dishes and decadent desserts.

Alternative options: Nebbiolo Wine Bar & Market, Blue Heron Bistro, The Verdict Bar & Grill

Stroll Through Historic Oregon City

Take a leisurely walk through historic Oregon City and explore the charming shops and boutiques that line the streets. Enjoy the picturesque views of the Willamette River and take in the historic architecture of this quaint city.

Alternative options: McLoughlin Promenade, End of the Oregon Trail Interpretive Center, Oregon City Municipal Elevator

Movie Night at the McMenamins Theater

Catch a movie at the McMenamins Theater, a historic theater that offers a unique movie-watching experience. Enjoy a drink from the bar while you watch a film in this cozy and eclectic setting.

Alternative options: Regal Hilltop Cinema, Milwaukie Cinema & Wunderland, Century Clackamas Town Center

Couples Cooking Class at Hipcooks

Sign up for a couples cooking class at Hipcooks and learn how to whip up delicious meals together. Bond with your partner while learning new culinary skills and enjoying a hands-on cooking experience.

Alternative options: Sur La Table, In Good Taste Cooking School, The Kitchen at Middleground Farms

Live Music at One of the Local Bars

Head to one of the local bars in Oregon City and enjoy live music performances by talented local artists. Sip on cocktails and enjoy the vibrant music scene in this lively city.

Alternative options: Arch Bridge Taphouse, The Highland Stillhouse, 508 Distillery & Bar

Spa Day at a Local Wellness Center

Indulge in a relaxing spa day at a local wellness center and treat yourselves to a massage or facial. Unwind and rejuvenate together in a peaceful and serene setting.

Alternative options: Happy Valley Day Spa, Hand & Stone Massage and Facial Spa, Zen Garden Day Spa

Sunset Picnic at Clackamette Park

Pack a picnic basket and head to Clackamette Park for a romantic sunset picnic by the river. Enjoy stunning views of the water and soak in the natural beauty of the park as you dine al fresco.

Alternative options: Willamette Falls, Mount Talbert Nature Park, Rivercrest Park

Paint Night at Live Laugh Love Art

Get creative at a paint night at Live Laugh Love Art, where you can enjoy a fun and interactive painting session with your partner. Sip on wine and unleash your inner artist in a relaxed and inspiring atmosphere.

Alternative options: The Loaded Brush, Muse Paintbar, Painting with a Twist

Stand-up Comedy Show at Harvey’s Comedy Club

Laugh the night away at a stand-up comedy show at Harvey’s Comedy Club. Enjoy a night of hilarious performances by top comedians and unwind with your partner in a fun and entertaining setting.

Alternative options: Helium Comedy Club, Curious Comedy Theater, The Siren Theater

So whether you’re looking for a romantic evening of fine dining, a fun and interactive cooking class, or a relaxing spa day, Oregon City has plenty to offer for your next date night. Take the time to plan a special night out with your partner and enjoy some quality time together away from the hustle and bustle of daily life. And remember, Wyndy is here to help you find a trusted and reliable sitter so you can relax and enjoy your date night worry-free. Book a sitter today and make your date night one to remember!