Portland Fall Date Ideas

When Summer plans begin to wind down, Portlanders get excited. In the PNW, it’s all about enjoying the lingering Summer warmth and embracing the cool night breeze, rainy Saturdays cozied with tea, and the changing colors that take your breath away. 

If you’re like the majority of us, you believe that Fall is the best time for dating. Before the holidays and the winter season, you crave finding a person with whom to share the quieter days. If you’ve had one too many short term winter flings, you might also think of Cuffing Season when Fall comes around. 

All we can say is we, at Fern Date, go wild for Fall. It is an amazing time to get outside, get close, and adventure with a potential match. Below, you’ll find outlined some of our favorite adventures like drive-ins, pumpkin patches, wineries, and hikes!

Fall Color Tours

One of the best ways to take advantage of Fall in the PNW is through spending time watching the landscape change. Here, the Fern Date team has mapped out some of Portland’s most beautiful places for an ideal date. 

  1. Hoyt Arboretum: Packed with 2,000 unique species of shrubs and trees, Hoyt Arboretum Provides a local passport to a globe’s worth of leaf-peeping. Grab a map and look for Japanese maples, magnolias, holly, fir and much more as you wander down one of the park’s 21 trails. 
  2. Pittock Mansion: Built over a century ago by the founder of Portland’s well-known paper, the Oregonian, Pittock Mansion’s 46-acre plot showcases the city’s natural beauty. Soak up the last blooms of the season, romantic views of the city and cascade Range, and explore miles of hiking trails that lead into Forest Park. 
  3. Maple Trail in Forest Park: The winding paths of Forest Park look their best in Fall. Enjoy the dewey ferns and well-trodden trails. This path in particular is an 8 mile loop that will give you plenty of time for conversation with your date. We suggest bringing snacks!
  4. Portland Japanese Gardens: The Portland Japanese Garden is amazing all year round, but it really stands out in Fall. This artfully curated park is absolutely beautiful in every direction. Our favorite marvels are the bonsai trees and the koi pond. They also have an intimate cafe and gift shop where you can spend some extra time enjoying the culture.
  5. Helicopter Tour: If the view from the ground isn’t enough, we recommend taking to the sky. Oregon Helicopter Tours get great reviews and can be a spectacular date when planned right. We recommend doing a shorter ride over the city during the day so you can see the foliage and the beautiful, Autumnal colors.

Snacks and Sips 

In Fall, the leaves change and so do our palettes. We want hot cider, smores, and soups, ideally while warming by the fire. Here, you’ll get the inside scoop on Portland’s best, most intimate date spots for Fall sips and snacks. 

  1. 1937 S’mores: America’s culinary driven, torch-fired s’mores company. See your gourmet s’more torched up in front of your eyes at their “cabin in the city” in downtown Portland. Fun fact, The name pays homage to the year that the first S’mores recipe was published in the Girl Scout’s newsletter “Tramping and Trailing.” 
  2. Schilling Cider House: With 50 taps dedicated to cider, you’re bound to find the best of Autumn apples at Schilling. They offer flights, food, and an intimate patio with table fire and rain cover. If you want to take advantage of autumn within the city limits, we definitely recommend adding Schilling to your agenda. 
  3. Hamacher Wines: A date in the Fall is incomplete without a trip out to Hamacher Wines. Open Wednesday – Sunday by appointment. Surround yourself with beautiful Fall scenery, while indulging in one of Hamacher’s exclusive wines. This is FernDate’s favorite wineries to take clients to and the owner and winemaker Eric is very personable and passionate about his work. 
  4. Loretta Jeans: Home to Portland’s favorite, locally owned pie shop. Open seven days a week (check out the website for hours). This spot is locally acclaimed with timeless favorites, daily breakfast specials, and seasonal delights. Don’t worry, we won’t tell if you start your holiday pie eating early this year.  
  5. Pip’s Original: Locally owned and family operated since 2013, our favorite donut and chai shop is located in NE portland. Open Thursday – Sunday from 8am-2pm, you won’t want to delay in getting in this line. Home to some of the best seasonal donuts and chai your taste buds could imagine. We recommend going when they open so you’re not waiting in the line for too long.
  6. Sugarpine Drive-in: Oregon’s premier destination drive-in restaurant on the banks of the Sandy River. This is most definitely one you won’t want to miss. It’s always seasonal and always delicious, which is reason enough to visit. Pro recommendation: don’t leave without trying the soft serve!

Festive Fall Favorites

Lots of our favorite activities peak in Fall. There’s no other time when it’s acceptable to walk through corn or hay. There’s no better time to make candles or snuggle up to a good book. Our list of Fall Favorites encompasses Oregon’s best. 

  1. Topaz Farms: Corn Maze + Fall Events: September 11-October 30th – 9am-6pm (Closed Mondays). Over 130 acres on Sauvie Island, Topaz Farm is committed to no-spray, regenerative practices. Fresh local fruits and vegetables and delicious, seasonal farm foods such as house-made ice cream, grilled corn, hand pies, grilled food, and picnic boxes are available in our open-air farm market and our farm bar serves local craft beer, cider, and wines.
    1. Corn Maze: $10 for adults (13+), $5 for kids (6-12) and seniors (65+). Free for kids 5 and under. Tuesdays, 2 for 1 deal! 
    2. Pumpkin Picking & free hayrides from 10am-4pm Fridays, Saturdays, and Sundays beginning on Friday, September 17th. 
    3. Visit the resident farm animals – miniature donkeys, miniature goats, Rita the dwarf cow, pigs, chickens, ducks, and a turkey. 
  2. Spirit of Halloweentown:  September 18th – October 31st. In 1998, the small city of St. Helens served as a backdrop to the Disney Channel Halloween classic “Halloweentown”, and each year thereafter they transform the Riverfront District into the Spirit of Halloweentown, a celebration of all things spooky. $35/per person for general admission tickets. 
  3. Candle Creation Bar: at Yo Soy Candle: Fall scents abound! Set an intention, choose a vessel, blend a scent, pour a candle, and create a positive ritual by crafting your very own I AM statement. Prices run $30-45 depending on your choice of vessel.
  4. Powell’s Books: It is never a better time to wander the expansive aisles of the nation’s largest independent bookstore and Portland’s favorite…best of all, it’s free! While you’re there, make sure to check out the Pearl Room, this room is off the beaten trail and is full of rare books – it’s definitely a hidden gem to impress your date. 
  5. Portland Farmers Markets: Portland Farmers Market is a nonprofit organization operating five vibrant farmers markets in Portland, Oregon. The markets provide a direct connection to more than 200 vendors with deep roots in Oregon and Southwest Washington, including farms, nurseries, bakeries, meat and seafood, cheeses, and specialty food producers. While some markets operate seasonally, the PSU Farmers Market is open year round on Saturdays (rain or shine) from 9:00am – 2:00pm. 
  6. Hood River Fruit Loop: The Hood River Fruit loop is located in the beautiful Hood River Valley at the foot of majestic Mt. Hood. The twenty-nine member stands offer you a variety of wines, fruits, vegetables, flowers, ciders, and food. While there are twenty-nine stands, they are not all open at the same times and dates. Please check the website for more specific information. 
  7. Smith Berry Barn: This lovely, quintessential destination is a Fall favorite you won’t want to miss. With a rotating variety of fruit and vegetable offerings, there is something for everyone. Plus, they have a darling gift shop equipped with an espresso and milkshake bar.

We hope to have convinced you to give Fall a try. With the right company, all of the date spots above really come to life. If you want to check out even more event ideas, we recommend looking to the city of Portland’s site to find Autumn event calendars. 

The truth is, Fall can be a really exciting time to build something new, but it can also be overwhelming. With the season changing, check in with yourself and what you want to find in the coming year. We’re confident that you can make this season full of joy and wonder. 

Wanting to get out this season but not sure where to find a date? Book a free consultation with us now to get started. 

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