A couple stands on a balcony overlooking a serene view, with one holding a glass of wine, framed by a curtain.

Lake Oswego, OR

Fall Guide

Fall is the perfect time to visit Lake Oswego for crisp air, changing leaves, and time outdoors. From scenic lakeside trails to wine tastings, there are endless things to do in Lake Oswego as the seasons shift. Whether here for a weekend getaway or planning a longer escape, make The Lakeshore Inn your home away from home.

A hand holds a glass of red wine, surrounded by bottles and glasses of wine in a warm-setting, suggesting a tasting or gathering.

Wine & Beer Tastings

This fall, sip your way through the best wine and beer in Lake Oswego. Taste Oregon wines at Domaine Serene and Willamette Valley Vineyards, or explore even more during the 11th Annual Lake Oswego Wine Walk. Beer lovers can stop by Breakside Brewing for award-winning craft brews. From wine walks to taprooms, Lake Oswego is the perfect place to raise a glass this season.

A charming shopping area with quaint buildings, storefronts, and a roundabout surrounded by greenery at dusk.

Shopping

The best shopping in Lake Oswego is steps from The Lakeshore Inn. Lake View Village offers the area's best boutiques and clothing stories, handmade gifts, and home decór. Some of our favorite shops include City Home, Golden, and the BOOKtique.

The Lakeshore Inn

Scenic Trolley Rides

September is the perfect time to ride the Willamette Shore Trolley. This vintage trolley takes you along the riverfront, through a historic tunnel built in 1921, and past Lake Oswego’s picturesque neighborhoods. The route follows a rail line dating back to the late 1800s, offering a unique way to experience the beauty and history of the area.

Three people are in traditional attire, two in colorful Bharatanatyam costumes and one in a hanbok, standing outdoors.

Cultural Xchange Festival

September 28th

Discover international flavors, handcrafted goods, and local nonprofits at the Cultural Xchange Festival. Enjoy traditional dance, music, martial arts demonstrations, and so much more - all without leaving Lake Oswego.

The image shows a row of trees with colorful autumn foliage next to a white fence under a clear sky.

Hiking

Looking for a fall hike near Portland? Step out from The Lakeshore Inn and enjoy Lake Oswego’s stunning autumn colors. Trails like Iron Mountain and Tryon Creek State Natural Area offer peaceful wooded paths, fall foliage, and a perfect escape just minutes from Portland.

A flaky croissant on a white plate and a cup of latte with latte art sit on a marble table, providing a perfect cafe scene.

Grab Coffee

There’s nothing like starting a crisp Oregon autumn morning with a perfect cup of coffee. Stop into St. Honoré Boulangerie for espresso and pastries, Peet’s Coffee for a classic brew, or Morse Coffee Company for locally roasted favorites.

The image shows a bookstore interior with wooden shelves and tables filled with books, and a person walking by.

Portland Book Festival

November 8th

Find your next great read at the Portland Book Festival, then unwind just minutes away from downtown with a relaxing stay at the Lakeshore Inn. The festival features on-stage discussions with over 100 authors, drop-in writing workshops, pop-up readings, an extensive book fair, and local food trucks - a city-wide celebration of Portland books and stories. Our lakefront balconies are the perfect spot to dive into a book.

Events