11 Cozy Fall Date Ideas in Portland

While many argue that summer is the season of love, we’re pretty partial to fall! Pumpkin patches, apple orchards and haunted houses—there is so much fun to be had this season. And, because fall is when Portland starts to get a little rainier, it makes for a pretty cozy backdrop to any date! 

We rounded up a few ideas for exciting, seasonal date activities in the area. From catching a ride on a local trolley to perusing books at a bookstore, autumn in Portland is the perfect place to fall in love! 


Explore the Portland Art Museum

Photo of the European Art Galleries at the Portland Art Museum courtesy of Portland Art Museum

On a cold, rainy fall day, there’s nothing better than spending an afternoon exploring a local museum with your partner. Founded in late 1892, the Portland Art Museum is the seventh-oldest museum in the country and the oldest in the Pacific Northwest. Step inside this historic art museum to see its internationally recognized permanent collection and ambitious special exhibitions. Afterward, stop by the Museum Store to pick out gifts together and grab a drink at the Museum Grounds Coffee Shop. 


Play a few games at Mox Boarding House

Board games plus great food equals a fantastic date with your sweetheart! Mox Boarding House is a unique board game library mixed with a classy restaurant perfect for fun dinners. Their Portland location offers Parisian-inspired architecture, an extensive game collection you can browse, buy and rent, and a full restaurant menu to enjoy. Stop in, pick out a game and play it as you snack on a delicious selection of pub-style food and drinks. 


Grab hot chocolate from Creo Chocolate

As the weather turns cooler, we’re swapping our cold beers for hot toddies and iced lattes for hot chocolate. If that’s you too, head to Creo Chocolate for a mug of the best hot chocolate in town with your partner this season. This small batch bean-to-bar chocolate factory makes seriously intense hot chocolate using a ganache that is made in-house from Ecuadorian cacao beans. While it isn’t as sweet as traditional hot chocolates, we promise it’s pretty amazing. While you’re there, don’t miss the chance to tour the factory and indulge in some tasty chocolate treats together! 


Check out a pumpkin patch

Pumpkin Patches in Pacific Northwest

Visiting a pumpkin patch in the fall is a classic for a reason! There’s just nothing like exploring local farms, picking out your pumpkin and enjoying every fall activity they have to offer this season, from corn mazes to hayrides. Click here to explore our favorite pumpkin patches in the area and make a plan to visit one before the season ends with your favorite person. 


Or visit an apple orchard

While we’re talking about fall farm activities, we can’t forget about apple orchards! Picking apples is a must in Oregon every fall, especially since the Portland area is full of fantastic apple orchards. We have a list of our favorites so be sure to stop by a few with your sweetheart this season. And if apple picking isn’t really your thing, don’t worry! Most apple orchards have farm stores where you can pick up bags of apples, apple cider, donuts, apple butter and more, without having to pick them yourself. 


Ride the Willamette Shore Trolley to Portland

Take in the scenic autumn views of the Willamette and surrounding features with your significant other on a ride aboard the Willamette Shore Trolley, which runs on Saturdays and Sundays from May to November. This vintage trolley travels from Lake Oswego into a dark tunnel, meandering through posh neighborhoods, along the Willamette into Portland’s Powers Marine Park, and then back to Lake Oswego. With low fares and stunning views, it’s the perfect seasonal date activity! 


Watch a movie at an independent theater

Portland’s film culture and industry is growing more and more each year, which means it isn’t exactly surprising that our area is full of fantastic independent movie theaters. This season, combine the classic “dinner and a movie” date and head to one of our local theaters, plenty of which offer a full menu that you can enjoy while you watch the film! Our favorites include Academy TheaterSt. Johns Theater & Pub, the Laurelhurst TheaterLiving Room TheatersMission TheaterPower Station TheaterHollywood Theatre, the Kennedy School, and many more. 


Browse Powell’s Books

Photo courtesy of Powell’s City of Books

Doesn’t fall make you want to spend the entire day in a bookstore? With over one million books in the store, Powell’s City of Books is accurately called a “city”, as this massive bookstore takes up an entire city block in the heart of the Pearl District. It’s the perfect place to shop for unique gifts, sit down with a cup of coffee at the cafe, or spend the day perusing books with your sweetheart. 


Get spooked at a haunted house

While creeping through a haunted house isn’t the first thing you picture when thinking about romantic activities, it can actually be a great opportunity to bond with your significant other! Stop by one of our local haunted houses this season—we have a list of current ones right here—and hold hands as you face all the horrors they have in store.  


Grab soup at Elephants Deli

We can’t think of a better lunch than soup on a chilly day! Elephants Delicatessen has some of the best soup in town, offering gourmet food and warm hospitality. Their menu includes comfort food classics, no matter which of their many Portland locations you visit. Macaroni and cheese, chicken pot pie, incredible sandwiches and, of course, several fantastic soup options. We’re partial to their famous Tomato Orange soup, but you can (and should) order a cup of each to share with your partner! 


Many flock to The Grotto to see the brilliant display of lights during the holiday season, but it is also an underrated destination during the fall! Surrounded by fir trees, colorful rhododendrons and other native plants, The Grotto is a 62-acre Catholic sanctuary welcoming more than 350,000 guests of all faiths each year. Take a trip with your partner to see the marble replica of Michelangelo’s famous Pietà carved into the base of a 110-foot cliff and ride the elevator (for a small fee) to the top of the bluff for a breathtaking, panoramic view of the area.


Have fun!

Do you have any fun fall date ideas that we missed? Let us know in the comments below! 

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