6 Things To Do in Portland this Memorial Day Weekend 2023

Portland, the City of Roses, is again busy and vibrant this Memorial Day Weekend 2023. It’s packed with fireworks and flowers and crazy adventures as unique as its people! Whether you’re a tourist or a local, there’s an endless array of Memorial Day Events for everyone in this eccentrically beautiful city.
Spend it with your family and friends, but also, don’t forget to remember what the day is all about – a time to remember and honor those who lost their lives in service of our country. So, amidst all the Memorial Day Weekend events you’re planning to go to, make sure you take time to think about all the fallen heroes who paved the way to our freedom.
We’ve rounded up some of the most fun things to do on Memorial Day in and around Portland and Gresham below. From camping to scavenger hunts, we got you!
Gresham Lion’s Club Memorial Day Weekend 2023 Trail Ride, May 27-29
Get away from the hustle and bustle of downtown Portland events and enjoy an amazing adventure in the woods at Gresham. Starting May 27 and ending on May 29, the Gresham Lion’s Club is hosting a Memorial Day Weekend Trail Ride. Although it’s ‘bring your own horse’ for the trail ride, you can also set up camp and enjoy the music, food, and fun on Saturday Night at Gresham Lion’s Shelter.
Camping is on a first-come, first-serve basis. So, if you want to camp out, come on early on Friday to set up camp.

Portland Rose Festival Opening Night & Fireworks and the CityFair @ Tom McCall Waterfront Park | May 26,2023 5pm to 11pm
Every year since 1907, Portland, also known as the “City of Roses,” holds the annual Portland Rose Festival to celebrate its heritage and unique community spirit. Although it’s a month-long celebration always held in June, the always festival always kicks off on Memorial Day.
So if you’re looking for fun things to do in Portland this weekend, get your family and friends together on a night of Carnival rides, good food, exhibits, music, kid-centric activities, and tons and tons of fireworks at Tom McCall Waterfront Park. The fireworks will start at 9:50pm.
It’s a party for all ages with a plethora of attractions and activities for everyone in the family!
The opening night and fireworks are on May 26, but the City Fair is open every weekend until June 11.

Oregon Wine Month
May is Oregon Wine Month, and it’s the perfect time to celebrate the state’s unique and diverse wine culture. With over 700 wineries in Oregon, it’s no wonder that the state produces some of the world’s finest wines, Pinot Noir being its most popular variety.
For the whole Month of May, wineries across the state offer a variety of events, such as tastings, vineyard tours, food and wine pairings, and educational seminars. Hit the road and explore Portland this Memorial Day for a winery tour. Here are some of the events you can join on Memorial weekend:
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- Memorial Weekend Celebration with Wood-fired Pizza at Knudsen Vineyards. Enjoy wood-fired pizza and wine while taking in stunning views from the Vineyard’s terrace on Saturday, May 27 and Sunday, May 28 from 11am to 3pm. Get a sneak peek of Kundsen’s new 2021 Family Series Chardonnay. Reservations are recommended for this limited seating event.
- Memorial Weekend Featured Tasting at Lange Estate Winery. For just $30, you can enjoy a tasting of their best wines, including Pinot Gris Reserve and their favorite Pinot Noirs from May 26-29 from 10am to 3pm.
- Spring Fling Flight at Flaneur Wines. Try out their newest releases, including their first-ever Grüner Veltliner and celebrated Pinot Meunier on May 27th, 28th, and 29th from 11am to 5pm. They’ll also have a special menu of light spring bites available.
- Indie Wine Mixer at The Bindery. This two-day event features 20 “indie” Oregon wineries, all in one location. Come taste wines made by some of Oregon’s newest winemakers. Tickets are $40 for one day only.
- Friday Night Live – Featuring Strawberry Roan at Oak Knoll Winery. Enjoy live music, charcuterie, and great wine at this 21-and-up event. Tickets are just $10 per person.
Farmers Market at Portland State University
Whether you’re a foodie, a supporter of sustainable agriculture, or just seeking a unique shopping experience, the PSU Farmer’s Market is the best place to experience Portland’s lively food scene. Open every Saturday from March through December, it’s the thing to do in Portland on Saturdays for both locals and tourists alike who are looking for a quick snack or a full grocery haul. You’ll find everything from locally sourced fresh produce to artisanal foods, handcrafted goods, plants & flowers, spirits, and more!
Aside from the delightful food options, the market also boasts live music, diverse activities for all ages, and various special events throughout the year. Swing by this Memorial Day Weekend and support small farmers and local businesses.
Subtle Intimacy: Here and There, exhibit at the Portland Japanese Garden
Catch Japan Institute’s inaugural Artist-in-Residence, Rui Sasaki’s exhibition at the Portland Japanese Garden on your Memorial Day Weekend getaway to Portland. Running from March 18th, 2023 – June 12th, 2023, “Subtle Intimacy: Here and There” features Sasaki’s site-specific glass art installations inspired by the beauty of the garden and the city.
Immerse yourself in Sasaki’s multi-sensory installations and explore your own relationship with nature. With its thought-provoking themes and stunning glass art, Subtle Intimacy: Here and There is a must-see for anyone looking to add a touch of art and culture to their Memorial Day weekend.

Urban Adventure Quest’s Amazing Scavenger Hunt Adventure, anytime!
Explore Oregon and learn about its local history with your family and friends with Urban Adventure Quest interactive scavenger hunt. This city-wide scavenger hunt will take you to Portland’s hidden gems and best sites, from the Pioneer Courthouse Square to the art district. It’s essentially a 2.4 miles of adventure guided by a smartphone!
The Price starts at $49 for a team of 2-5 people. Visit their website for more information.
The City of Roses has a lot of Memorial Day activities and weekend events in store for you this 2023. But if you need some downtime and want to get away from the crazy festivities of the city, head to Ponderosa Inn at Gresham. Just 15 miles away from downtown Portland, our cozy yet immaculate rooms await you and your family. Get the best of both worlds at Ponderosa Inn – the scenic landscapes and parks of Gresham and the vibrant city of Portland.