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15 Aug 2025
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7 Best Places For Weekend Trips From Gresham, OR

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

  • Trip Point Pin1

    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.
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  • Mount Hood is perfect for outdoor enthusiasts, offering year-round activities such as skiing, snowboarding, hiking, and picturesque alpine lakes.
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  • Hood River is renowned for its vibrant downtown, craft breweries, windsurfing on the Columbia River, and access to beautiful fruit orchards and vineyards.
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  • Trip Point Pin4

    Cannon Beach

    Cannon Beach features iconic coastal scenery with Haystack Rock, wide sandy beaches, art galleries, and a charming seaside town atmosphere.
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  • Trip Point Pin5

    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.
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  • Astoria boasts a rich maritime history, Victorian architecture, museums, waterfront views, and access to the scenic Oregon Coast and Columbia River.
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  • Bend offers a vibrant blend of outdoor adventure, craft breweries, mountain biking, hiking, river activities, and stunning views of the Cascade Mountains.
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Restaurants

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    Multnomah Falls Lodge Restaurant

    4.5
    $$$$

    Multnomah Falls Lodge Restaurant

    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
    $$$$
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    Rimrock Café at Timberline Lodge

    4.1

    Rimrock Café at Timberline Lodge

    Experience mountain dining inside the iconic Timberline Lodge on Mount Hood, known for its alpine setting and rustic charm.
    4.1
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    Solstice Wood Fire Pizza

    4.5
    $$$$

    Solstice Wood Fire Pizza

    Located in Hood River, this spot offers creative wood-fired pizzas with locally sourced ingredients and views of the Columbia River.
    4.5
    $$$$
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    Stephanie Inn Dining Room

    4.7

    Stephanie Inn Dining Room

    A fine dining experience steps from Cannon Beach, featuring dishes crafted from local seafood and produce with ocean views.
    4.7
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    Bowpicker Fish & Chips

    Bowpicker Fish & Chips

    This Astoria favorite serves legendary fish and chips from a converted boat, making it a must-visit for its unique setting and delicious food.
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Hotels

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    Timberline Lodge

    9.1

    Timberline Lodge

    This National Historic Landmark on Mount Hood offers rustic elegance, unique architecture, and panoramic mountain views.
    9.1
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    McMenamins Edgefield

    9

    McMenamins Edgefield

    A historic hotel in Troutdale with quirky art-filled rooms, an on-site brewery, soaking pool, and live music events.
    9
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    Cannon Beach Hotel

    Cannon Beach Hotel

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

    4.8

    The Silo Suites at Abbey Road Farm

    Stay in luxurious converted grain silos on a working farm in Oregon wine country, offering a truly unique lodging experience.
    4.8
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    Hotel Elliott

    3.6

    Hotel Elliott

    A boutique hotel in downtown Astoria featuring a rooftop patio, historic charm, and beautifully appointed themed rooms.
    3.6
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Local Events & Happenings

  • Event Icon

    Pixies w/ Spoon

    Pixies w/ Spoon

    The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
    Map IconMcMenamins Historic Edgefield Manor in Troutdale (9.08 mi)
    Calendar Icon31 Aug 2025
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    Teddy Swims

    Teddy Swims

    The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
    Map IconMcMenamins Historic Edgefield Manor in Troutdale (9.08 mi)
    Calendar Icon4 Sep 2025
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    Gregory Alan Isakov w/ Dean Johnson

    Gregory Alan Isakov w/ Dean Johnson

    The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
    Map IconMcMenamins Historic Edgefield Manor in Troutdale (9.08 mi)
    Calendar Icon8 Sep 2025
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    Modest Mouse w/ The Flaming Lips

    Modest Mouse w/ The Flaming Lips

    The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
    Map IconMcMenamins Historic Edgefield Manor in Troutdale (9.08 mi)
    Calendar Icon11 Sep 2025
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    The Flaming Lips

    The Flaming Lips

    The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
    Map IconMcMenamins Historic Edgefield Manor in Troutdale (9.08 mi)
    Calendar Icon12 Sep 2025
    Picture for The Flaming Lips
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    Haim

    Haim

    The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
    Map IconMcMenamins Historic Edgefield Manor in Troutdale (9.08 mi)
    Calendar Icon18 Sep 2025
    Picture for Haim
  • Event Icon

    Big Thief

    Big Thief

    The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
    Map IconMcMenamins Historic Edgefield Manor in Troutdale (9.08 mi)
    Calendar Icon20 Sep 2025
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Travel Gems from Reddit

  • Reddit Icon

    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

    In Gresham area for the weekend, what to do?

    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

    /r/askportland
  • Reddit Icon

    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 is it like living in Gresham?

    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...

    /r/askportland
  • Reddit Icon

    Best Mom/Daughter spa weekend getaway within ~two hours of Portland? Looking For My mom is flying in to visit, probably early March, to take my depressed ass out to celebrate ...

    Best Mom/Daughter spa weekend getaway within ~two hours of ...

    Best Mom/Daughter spa weekend getaway within ~two hours of Portland? Looking For My mom is flying in to visit, probably early March, to take my depressed ass out to celebrate ...

    /r/askportland
  • Reddit Icon

    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

    What are your favorite things past 82nd?

    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

    /r/askportland
  • Reddit Icon

    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

    Where would you stay for a quick weekend trip?

    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

    /r/AskChicago

Music for Your Journey

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    Edward Sharpe & The Magnetic Zeros - Home

    Edward Sharpe & The Magnetic Zeros - Home

    A feel-good anthem for road trips, celebrating the joy of traveling and finding new places.
    Listen on Spotify
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    Fleetwood Mac - Go Your Own Way - 2004 Remaster

    Fleetwood Mac - Go Your Own Way - 2004 Remaster

    Classic rock vibes to inspire adventure and freedom on the open road.
    Listen on Spotify
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    Talking Heads - Road to Nowhere

    Talking Heads - Road to Nowhere

    Uplifting and quirky, perfect for driving through new landscapes with a sense of wonder.
    Listen on Spotify
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    Rusted Root - Send Me on My Way

    Rusted Root - Send Me on My Way

    Light-hearted and whimsical, great for cruising scenic highways and setting a fun tone.
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    Rascal Flatts - Life is a Highway

    Rascal Flatts - Life is a Highway

    An energetic track that captures the thrill and freedom of a road trip adventure.
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    George Ezra - Budapest

    George Ezra - Budapest

    A catchy melody with a sense of exploration and traveling to unknown destinations.
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    Bon Iver - Holocene

    Bon Iver - Holocene

    Calming and reflective, ideal for soaking in the natural beauty along your route.
    Listen on Spotify
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    Eagles - Take It Easy - 2013 Remaster

    Eagles - Take It Easy - 2013 Remaster

    A laid-back classic that complements the relaxed pace of a scenic drive.
    Listen on Spotify
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    Empire of the Sun - Walking On A Dream

    Empire of the Sun - Walking On A Dream

    Dreamy and upbeat, setting an adventurous and optimistic mood for your travels.
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    Willie Nelson - On The Road Again - Live

    Willie Nelson - On The Road Again - Live

    A timeless road trip favorite, perfect for the excitement of hitting the road.
    Listen on Spotify
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