It may not be Jenne Road in Vermont, but Portland, OR, has a pretty incredible fall. Maybe you’re already mourning the blooms at the International Rose Test Garden or have tried every chai variation at Pip’s Original Doughnuts, but a Portland autumn is nothing to pass over. Known for rain, an incredible food scene, and the birthplace of hipsters, this Pacific Northwest city is also the top place to live in Oregon.
Whether you just moved into your rental home and this is your first PDX fall or you’re apartment hunting and find yourself in search of the perfect cocktail lounge to run to when the rain strikes, we have you covered! Perfect for outdoor enthusiasts, art lovers, thrift shoppers, new residents, longtime locals, and visitors alike, we guarantee you’ll add at least one of our Portland fall recommendations to your list.
1. Night at the museum
From curious children to amused adults, the Oregon Museum of Science and Industry (OMSI) truly has something for everyone. On your visit, you’ll find hands-on exhibits, fascinating science demonstrations, and engaging IMAX films – all great for interactive learning. Did you also know you can go at night? Occurring on the last Wednesday of every month, OMSI After Dark is a super cool experience open to ages 21+. Here you’ll find local vendors, artisans, and rotating science demos, so be sure to put this on your fall calendar.
2. Unleash your creativity
If you’ve just moved to Portland and want to meet new people or are looking to change up the routine and learn a new skill, we cannot recommend a creative class enough. WildCraft Studio School offers craft, textiles, studio art, Native art, and nature workshops in the North Mississippi and inner SE Division neighborhoods. “For 11 years, we've worked with Portland's most talented and experienced artists, craftspeople, naturalists, and educators to make creativity accessible to curious adult learners, explains founder Chelsea Heffner. We especially suggest checking out their calendar for a list of upcoming workshops like Sashiko Japanese mending, cattail weaving, or mushroom cultivation – you’re sure to find something that piques your interest!
If you’ve had glass art on your to-do list, however, Marvelous Mosaic offers several engaging workshops in mosaic art, fusing, and stained glass. “Whether you’re a seasoned artist or a curious beginner, this retreat provides the perfect space to explore your creative potential,” says owner and mosaic artist Kory Dollar. Here you’ll find top-quality supplies and expert guidance to help you “craft stunning pieces of art while making new friends in the vibrant local community.”
3. Hike Portland’s beautiful nature
The PNW is known for its nature, so be sure to put at least one hike on your to-do list this autumn. One of our favorites is a hike through Washington Park. First, start at the Hoyt Arboretum, and continue on a loop that brings you through the Fir Trail, Redwood Trail, and the Overlook Trail. Then, continue east along the Wildwood Trail, and finally to the International Rose Test Garden. Don’t forget to check out the Redwood Observation Deck, breathe in the lush PNW air, and enjoy the views.
4. Find a new fave food
In Portland they’re called food carts, not food trucks, and they’re amazing. Located just north of the Moda Center, Cartside Food Carts offers eight incredible food carts to choose from. Whether you’re in the mood for Mexican, Mediterranean, or Texas BBQ, this spot is sure to satisfy your cravings. They also have a full-service bar alongside heated and covered deck and patio spaces perfect for even theFc chilliest and rainiest of fall weather. “Whether you're looking for a lively sports bar, a family-friendly and dog-friendly food cart pod, or a fun spot with routine game nights, karaoke, and live music, Cartside Food Carts is a worthwhile visit for Portlanders and visitors of Rose City,” says marketing coordinator Nicole Mormann.
Another great food cart spot is Happy Valley Station Food Carts located in the Happy Valley neighborhood. This location features eighteen different carts with cuisine from all over the world like Thai, Indian, Korean, Peruvian, and Japanese to name a few. They also have an “amazing 45 Tap Beer / Wine / Cider Bar that operates year round,” to pair with your meals, says owner Valerie Hunter. Did we mention they also have desserts? If you’re not in the mood for a full meal or just want to stop for a sweet treat, there are carts serving boba, cake, cupcakes, and other delicacies as well.
5. Immerse yourself in Portland’s foodie scene
Still hungry? A great way to get a lay of Portland’s foodie land and stuff your stomach is to take a walking food tour. Portland By Mouth Food Tours offers the tastiest ways to experience Portland as you’ll be sampling some of Portland’s finest bites while learning lots about local chefs. Between eating, you’ll also be “strolling through Portland’s unique and charming neighborhoods, taking time to admire murals, architecture and talk about all things Portland, both past and present,” describes owner Sherri Brown. Be sure to add this unique tour to your list of things to do this fall, especially if you're new to the city, love food, and want to try new bites.
6. Take a thrift trip
The PNW is pretty known for having large sustainability initiatives, and one great way is to shop second-hand. Portland has several incredible vintage stores alongside traditional thrift shops, but if you’re looking for an easier way to shop second-hand, we recommend checking out a consignment store. Located in the heart of the Alberta arts district, Modo Boutique is a “carefully curated consignment clothing store with top designer labels to independent and one-of-a-kind finds,” describes co-owners Allison Fordham and Myla Crowell. Consignment stores are like a thrifting life hack since you don’t have to sift through as many potentially drab pieces – “It's like having access to the world's most amazing closet, filled with only the cutest and most exciting pieces,” says Allison and Myla. With the autumn weather in swing and winter well underway, consider taking a consignment store trip for a whole new wardrobe, or at least a few new (to you) pieces.
7. Brunch at a beloved spot
Brunch is by far one of the best meals, and beloved Portland spot Besaw's serves up some of the best. Located in the Slabtown neighborhood, Besaw's not only has an award-winning brunch, but they’re also one the oldest restaurants in Portland. Since 1903, people have been loving their friend chicken and waffles and Dungeness crab benedict – favorites recommended to us by owner Ramzy Hattar.
8. Wander through the art and community market
A trip to the Portland Saturday Market is a Portland must, especially in the crisp fall weather.
Occurring only on Saturdays, this outdoor market has several local vendors offering everything from henna, to hand-bound leather journals, to mosaic art jewelry. This is such a great spot to support small businesses creating handmade arts, crafts, and food in the PDX area.
If you’re a current Saturday Market vendor or are looking to expand your small business, Bricks Need Mortar might be able to help. Sarah Shaoul founded this company with the goal of leading “small businesses to access resources, gain skills and facilitate collaboration so [they] can thrive into the future.” Small Shops Big Hearts is one of their programs focused on helping consumers be intentional about how and where they spend their money by making it easy to find businesses owned and operated by people who live in local Portland communities. Especially if you like to start planning your holiday shopping early, add their Win Big event to your things to do this fall. This holiday event not only “makes shopping fun, [but also features] over 100 prizes including air travel and vacation stays,” says Sarah.
9. Grab a pint
Besides the lush nature, the PNW is also home to some of the best breweries. One of our favorites is Old Market Pub & Brewery located in the Garden Home neighborhood. This spot is the perfect fall “destination for handmade pizzas, craft ales made in-house, and family-friendly fun,” says PR marketing manager Savannah Bigley. This long-time neighborhood staple has it all from happy hour deals to weekend brunch to shuffleboard and pool. We especially suggest going on a beautiful autumn day to enjoy their dog-friendly patio with your pup. Even if you don’t have one, we love enjoying a pint outside while asking to pet every, single, puppy.
10. Picnic at the park
The iconic bookstore, Powell’s, is on most Portland to-do lists, but we recommend picking up a new read and heading to the park. Just grab a friend or two (new or old) and head to Tom McCall Waterfront Park. On your short walk through downtown, pick up lunch to make this silent book club more of a picnic, and enjoy the most perfect fall afternoon.
11. Shop local
Did you know Portland also has some of the best boutiques? One of our favorites in Frock Boutique located just a little north of the city in the Alberta Arts neighborhood. This locally owned and operated store “features whimsical clothing, jewelry and gifts by designers and brands from near and far,” says co-owner Allison Wykhuis. With their eclectic selection, you’re sure to find something you want to bring home on your next shopping trip.
Although we love shopping for ourselves, if you’re in the market for a gift look no further than With Love, From PDX. Their variety gift boxes are full of Portland-made goods and products from local small businesses and make the perfect housewarming gift. Whether you’re hosting a baby shower at your new place or attending a mid-autumn festival, their boxes are sure to put a smile on everyone’s face.
12. Tour (guide) the city
Have a little one? The Urban Tour Group provides free – yes free – city tours of downtown Portland for students in grades 3-5. Here children will get the opportunity to learn about Portland’s history, architecture, art, and culture in one of three two-hour tours! Whether you just moved or are a longtime Portland inhabitant, they’re looking for adults to volunteer as guides – training provided! This is such a great way to get involved in the community and meet a new group of people, adults and kids alike.
13. Enjoy local art
Located near the Cedar Mill Community Library, the Village Gallery Of Arts “has existed to ignite the joy of learning, creating, and appreciating art in our community.” Whether you’re shopping for a new piece for your Portland, OR home or just want to check out the local art scene, this is the spot. They support both professional and emerging artists and also offer a variety of classes and workshops open to all ages and abilities should you find yourself inspired to create.
14. Caffeinate up
It wouldn’t be a PDX to-do list without the mention of coffee. Located in North Portland, The Stacks Coffeehouse is not only a beloved coffee spot, but it also doubles as a community library. They serve up “delicious coffee from local roaster Pastime Coffee, tea from Smith Teamaker, and house-made chai, along with a wide variety of pastries, and their specialty -- Austin-style breakfast tacos,” says co-owner Mary Milstead. This special spot has floor-to-ceiling bookshelves with reads for everyone to borrow – all on the honor system. If you’re looking to meet new people alongside your cup of joe, check out their weekly writing cafe night or monthly craft night.
15. Sip on a craft cocktail
To finish out this list, we couldn’t forget two of our favorite Portland cocktail spots. After all, the PDX does have a pretty incredible bar scene. Whether you’re going with your friends, out with family, on a date night, or having a solo night out, you have to go to at least one of these this fall.
Located in the historic St Johns district, Havalina specializes in “handcrafted, creative cocktails, friendly conversation, and live events featuring local artists,” says owner Ezra Holbrook. They pride themselves not only on tasty drinks, but also on their diverse, inclusive, and welcoming atmosphere making it the perfect place for everyone.
If you find yourself in East Portland, check out Lulu Bar! This location is known for its creative cocktails, warm ambiance, and attentive service. The cocktail menu includes signatures such as their passion tea lemonade, but you can also ask the bartender to mix up a daily special. So, “Whether you're looking for a cozy place to unwind with friends or a lively evening out, Lulu offers an exceptional experience that combines innovative drinks with a relaxed, inviting atmosphere,” says owner Vijay Kumar.
