7 Best Places For Weekend Trips From Gresham, OR

26 May 2026Updated last time

Weekend Getaway Itinerary Overview from Gresham, OR

Embark on an unforgettable weekend adventure starting from Gresham, Oregon, as you explore some of the most scenic and diverse destinations in the Pacific Northwest. Begin your journey at the majestic Columbia River Gorge, where waterfalls and panoramic vistas await you. Head toward the thrilling peaks of Mount Hood, perfect for both winter sports and summer hiking. Not far away, the picturesque town of Hood River offers charming streets, craft breweries, and exhilarating water sports on the Columbia River.

Continue west to the breathtaking Cannon Beach, where Haystack Rock rises from the sandy shore, inviting you to relax and explore local art galleries and cafes. Immerse yourself in the lush forests and spectacular waterfalls of Silver Falls State Park on the legendary Trail of Ten Falls. In the historic city of Astoria, experience maritime heritage, climb the Astoria Column, and sample fresh seafood by the water. Conclude your trip in Bend, nestled in the high desert, where endless outdoor adventures, vibrant nightlife, and stunning mountain views blend seamlessly. This itinerary promises an enriching blend of nature, history, and recreation for an unforgettable weekend escape.


Recommended Activities

  • 1

    Columbia River Gorge

    The Columbia River Gorge offers breathtaking waterfalls, scenic hiking trails, and stunning viewpoints, making it a paradise for nature lovers and photographers.
  • Mount Hood is perfect for outdoor enthusiasts, offering year-round activities such as skiing, snowboarding, hiking, and picturesque alpine lakes.
  • Hood River is renowned for its vibrant downtown, craft breweries, windsurfing on the Columbia River, and access to beautiful fruit orchards and vineyards.
  • 4

    Cannon Beach

    Cannon Beach features iconic coastal scenery with Haystack Rock, wide sandy beaches, art galleries, and a charming seaside town atmosphere.
  • 5

    Silver Falls State Park

    Silver Falls State Park is famous for its 'Trail of Ten Falls,' where you can hike past and even behind stunning waterfalls amidst lush forest settings.
  • Astoria boasts a rich maritime history, Victorian architecture, museums, waterfront views, and access to the scenic Oregon Coast and Columbia River.
  • Bend offers a vibrant blend of outdoor adventure, craft breweries, mountain biking, hiking, river activities, and stunning views of the Cascade Mountains.

Restaurants

  • Picture for Multnomah Falls Lodge Restaurant

    Multnomah Falls Lodge Restaurant

    53000 Historic Columbia River Hwy, Corbett, OR 97019, USA
    Dine inside a historic lodge at the base of a breathtaking waterfall in the Columbia River Gorge, offering Pacific Northwest cuisine and stunning views.
    4.5
    $$$$
  • Picture for Rimrock Café at Timberline Lodge

    Rimrock Café at Timberline Lodge

    Timberline Lodge, 27500 W Leg Rd, Government Camp, OR 97028, USA
    Experience mountain dining inside the iconic Timberline Lodge on Mount Hood, known for its alpine setting and rustic charm.
    4.1
  • Picture for Solstice Wood Fire Pizza

    Solstice Wood Fire Pizza

    501 Portway Ave, Hood River, OR 97031, USA
    Located in Hood River, this spot offers creative wood-fired pizzas with locally sourced ingredients and views of the Columbia River.
    4.5
    $$$$
  • Picture for Stephanie Inn Dining Room

    Stephanie Inn Dining Room

    2740 Pacific Ave, Cannon Beach, OR 97110, ארצות הברית
    A fine dining experience steps from Cannon Beach, featuring dishes crafted from local seafood and produce with ocean views.
    4.7
  • Picture for Bowpicker Fish & Chips

    Bowpicker Fish & Chips

    1634 Duane St, Astoria, OR 97103, United States
    This Astoria favorite serves legendary fish and chips from a converted boat, making it a must-visit for its unique setting and delicious food.

Hotels

  • Timberline Lodge

    27500 E Timberline Road, Government Camp, OR 97028, United States

    This National Historic Landmark on Mount Hood offers rustic elegance, unique architecture, and panoramic mountain views.
  • McMenamins Edgefield

    2126 SW Halsey St, Troutdale, OR 97060, United States

    A historic hotel in Troutdale with quirky art-filled rooms, an on-site brewery, soaking pool, and live music events.
  • Cannon Beach Hotel

    1116 S Hemlock St, Cannon Beach, OR 97110, United States

    A charming, boutique coastal inn with vintage-inspired decor, just steps from Haystack Rock and the oceanfront.
  • The Silo Suites at Abbey Road Farm

    10280 NE Oak Springs Farm Rd, Carlton, OR 97111, USA

    Stay in luxurious converted grain silos on a working farm in Oregon wine country, offering a truly unique lodging experience.
  • Hotel Elliott

    357 12th St, Astoria, OR 97103, United States

    A boutique hotel in downtown Astoria featuring a rooftop patio, historic charm, and beautifully appointed themed rooms.

Local Events & Happenings

  • Picture for The Black Keys

    The Black Keys

    McMenamins Historic Edgefield Manor in Troutdale (8.51 mi)28 May 2026
    The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
  • Picture for Sierra Ferrell

    Sierra Ferrell

    McMenamins Historic Edgefield Manor in Troutdale (8.51 mi)31 May 2026
    The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
  • Picture for Bob Dylan w/ Lucinda Williams

    Bob Dylan w/ Lucinda Williams

    McMenamins Historic Edgefield Manor in Troutdale (8.51 mi)5 Jun 2026
    The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
  • Picture for Rainbow Kitten Surprise w/ Spacey Jane

    Rainbow Kitten Surprise w/ Spacey Jane

    McMenamins Historic Edgefield Manor in Troutdale (8.51 mi)13 Jul 2026
    The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
  • Picture for Charley Crockett

    Charley Crockett

    McMenamins Historic Edgefield Manor in Troutdale (8.51 mi)15 Jul 2026
    The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
  • Picture for Bob Moses w/ Cannons

    Bob Moses w/ Cannons

    McMenamins Historic Edgefield Manor in Troutdale (8.51 mi)16 Jul 2026
    The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
  • Picture for Cake

    Cake

    McMenamins Historic Edgefield Manor in Troutdale (8.51 mi)25 Jul 2026
    The event will take place at McMenamins Historic Edgefield Manor in Troutdale.

Travel Gems from Reddit

  • In Gresham area for the weekend, what to do?

    /r/askportland

    As the title says, Im in Gresham for the weekend and looking for fun activities to do in the area Tonight, best bar/socializing scene Tomorrow

  • What is it like living in Gresham?

    /r/askportland

    You probably wont have a corner ... does service Gresham, not super frequent and its quite long, but it does go out there. There are so many fun places to explore in Oregon ou...

  • What are your favorite things past 82nd?

    /r/askportland

    159 votes, 157 comments. Pretty low stakes question here, just trying to get East Portland some love. We all know about the fabulous inner areas of

  • Where would you stay for a quick weekend trip?

    /r/AskChicago

    Thanks in advance for any advice! I am coming to Chicago in April for the Phillies/Cubs series. We are going Thur night to Sun morning, so only going

  • Spent the weekend exploring Columbia River Gorge, Mt Hood and Cannon Beach

    /r/Portland

    Oregon 4-Day Itinerary: Gorge Mt. Hood Silver Falls Coast Portland Or Should I Reverse It? ... Stops between cannon beach and Portland.

  • Oregon 4-Day Itinerary: Gorge Mt. Hood Silver Falls Coast Portland Or Should I Reverse It?

    /r/oregon

    Visiting Oregon for Memorial Day weekend (May 2327). Flying in/out of PDX, renting a car. Were doing a loop: Day 1: Columbia River Gorge + Hood

  • Columbia River Gorge & Mt Hood day trip advice - what can we add or skip?

    /r/askportland

    How about limiting to one waterfalls (get that Multnomah permit if you can, since theyll all be packed on an August weekend), and the Vista House for the Gorge. Then find one ...

  • Advice for short Oregon trip I am making soon.

    /r/oregon

    Then of course theres Silver Falls State Park which is hard to go wrong with. On Mt. Hood theres Ramona Falls which requires fording a river but 100% worth it, also Mirror Lak...

  • Places to visit & things to do in Oregon..

    /r/oregon

    1 day Columbia Gorge, Multnomah Falls, Hood River then up the backside of Mt Hood and back to Portland. 1 day drive to Astoria and visit where you want on the Oregon Coast dow...

  • First trip to Oregon - need help with itinerary

    /r/oregon

    Go from there over to Bend and Sisters and head from there to Hood River. Finish your trip up exploring the Columbia Gorge as you head to Portland. ... At the minimum I would ...

  • Critique my Oregon Vacay Itinerary

    /r/oregon

    Hi everyone -- I've never been to Oregon, and my husband and I are doing a 7-day trip in June. I'd love to get everyone's thoughts on our schedule