Hillsdale

Parks, Trails & Green Space

Top 5 places to get outside

• Gabriel Park — A sprawling 90-acre park on Hillsdale’s western edge, Gabriel Park is known for its off-leash dog area, sports fields, skatepark, walking paths, and wooded nooks—great for outdoor gatherings, tennis, or a simple stroll.

• Hillsdale Park — A quieter, wooded greenspace just off SW Sunset Blvd, this pocket park has a playground, open fields, and shaded picnic areas, making it a favorite for families.

• DeWitt Park — Tucked in the neighborhood core, DeWitt is compact but well-used, offering a community garden, grassy spaces, and benches along the walking path.

• George Himes Park — Bordering Hillsdale, this linear park is known for its forested trails connecting down to SW Terwilliger Blvd—perfect for a peaceful nature hike within the city.

• SW Trail #3 — A segment of Southwest Portland’s famous urban trail network passes through Hillsdale, connecting parks and hidden stairways for walkers and runners.

Coffee Shops

Top 5 places for a coffee

• The Baker & Spice — A celebrated Hillsdale bakery and coffeehouse, popular for artisan pastries, breakfast sandwiches, and carefully pulled espresso drinks. Known as a bustling community gathering spot in the heart of the village center.

• Java Man — A classic neighborhood coffeehouse with relaxed, lived-in charm. Offers locally roasted coffee, bagels, and outdoor seating right on Capitol Highway.

• Blue Kangaroo Coffee Roasters — Local micro-roaster known for house-roasted beans, pour overs, and a cozy indoor space with rotating local art. Loved by both students and commuters.

• Ovation Coffee & Tea — Bright, modern café with an emphasis on espresso classics, loose-leaf teas, and high-quality pastries. Enjoy a casual coffee in a crisp, airy setting.

• Café Rowan — A warm café offering specialty coffee drinks and fresh baked goods, with a welcoming atmosphere and friendly baristas.

Restaurants & Food Carts

Top 5 places for a bite to eat

• Laughing Planet Cafe (Hillsdale) — OG location of this PNW healthy-eats mini-chain, serving burritos, bowls, and salads with a focus on local ingredients. Family-friendly and always buzzing.

• Pizzicato Pizza (Hillsdale Village) — Portland’s hometown pizza name, Pizzicato serves thin-crust pies, salads, and craft beers in a modern-casual setting. Known for their creative pies and quick lunch specials.

• Sasquatch Brewing Co. — Hillsdale — Local microbrewery with in-house brews, hearty pub fare, and wood-fired pizza. A gathering spot for families and beer lovers with a dog-friendly patio.

• Bertha’s Place — A beloved Hillsdale breakfast and lunch nook, Bertha’s is known for down-to-earth classics—scrambles, pancakes, and robust coffee—served in cheerful surroundings.

• Hillsdale Food Park — This locally-run cart pod features rotating vendors, from Thai to burgers to vegan eats. Shady picnic tables make it a dependable choice for groups and families.

Bars

Top 5 places for a drink

• Sasquatch Brewing Co. — A cornerstone for craft beer in the neighborhood, this warm, rustic taproom offers a rotating tap list, house ciders, and a full menu. Patio seating welcomes dogs and groups.

• John’s Marketplace — Hillsdale — A beer-lover’s haven with hundreds of bottles and cans, plus an in-house taproom pouring rare Oregon brews. Enjoy casual indoor tables and a friendly, chatty atmosphere.

• Tavern on Kruse — Just bordering Hillsdale, Tavern on Kruse is known for local beers, craft cocktails, and a comfortable, upscale bar fare menu. Great for after-work or date nights.

• Gabriel Park Pub — A neighborhood favorite drawing regulars for microbrews, bar food, and trivia. Unpretentious and welcoming with a muraled patio.

Things To Do

Top 5 things worth your time

• Hillsdale Farmers Market — Held every Sunday year-round in the Rieke School parking lot, this market draws neighbors for farm produce, local specialties, and friendly community energy.

• Hillsdale Library Events — The local Multnomah County Library branch hosts author talks, kids’ story hours, and craft workshops each week. Programs for every age fill the event calendar.

• Southwest Trails Urban Hikes — Join guided walks or explore at your own pace on the marked SW Urban Trail network, winding through green belts, parks, and hidden stairways.

• Gabriel Park Skatepark — A destination for boarders and BMX kids, this outdoor park offers varied ramps, rails, and bowls, plus friendly vibes and good shade.

• Yoga Union SW — Neighborhood studio offering daily classes for all levels—hatha, vinyasa, and restorative—plus community events and mindful workshops.

Community Resources

Local services & organizations

• Hillsdale Neighborhood Association — Active neighborhood group hosting annual cleanups, block parties, and monthly meetings. Connects residents with city services and local advocacy.

• Hillsdale Community Center — Run by Portland Parks & Rec, this center has fitness classes, after-school programs, and meeting rooms for neighborhood events.

• Multnomah County Library — Hillsdale Branch — Welcoming community space with study rooms, robust kids’ programming, and cultural events. A year-round gathering spot.

• Rieke Elementary School Gym & Fields — Used for sports leagues and public recreation, especially in evenings and summers.

• Hillsdale Post Office — Central USPS branch at the heart of the commercial district, serving residents and local businesses.

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