Oregon

26 May 2026Updated last time

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

1
Columbia River Gorge
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The Columbia River Gorge offers breathtaking waterfalls, scenic hiking trails, and stunning viewpoints, making it a paradise for nature lovers and photographers.
2
Mount Hood
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Mount Hood is perfect for outdoor enthusiasts, offering year-round activities such as skiing, snowboarding, hiking, and picturesque alpine lakes.
3
Hood River
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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.
4
Cannon Beach
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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
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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.
6
Astoria
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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.
7
Bend
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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.

Restaurants

Multnomah Falls Lodge Restaurant
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4.5
$$$$
Multnomah Falls Lodge Restaurant
Dine inside a historic lodge at the base of a breathtaking waterfall in the Columbia River Gorge, offering Pacific Northwest cuisine and stunning views.
4.5
$$$$
Rimrock Café at Timberline Lodge
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4.1
Rimrock Café at Timberline Lodge
Experience mountain dining inside the iconic Timberline Lodge on Mount Hood, known for its alpine setting and rustic charm.
4.1
Solstice Wood Fire Pizza
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4.5
$$$$
Solstice Wood Fire Pizza
Located in Hood River, this spot offers creative wood-fired pizzas with locally sourced ingredients and views of the Columbia River.
4.5
$$$$
Stephanie Inn Dining Room
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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
Bowpicker Fish & Chips
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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.

Hotels

Timberline Lodge
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4.55
Timberline Lodge
This National Historic Landmark on Mount Hood offers rustic elegance, unique architecture, and panoramic mountain views.
4.55
McMenamins Edgefield
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4.5
McMenamins Edgefield
A historic hotel in Troutdale with quirky art-filled rooms, an on-site brewery, soaking pool, and live music events.
4.5
Cannon Beach Hotel
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Cannon Beach Hotel
A charming, boutique coastal inn with vintage-inspired decor, just steps from Haystack Rock and the oceanfront.
The Silo Suites at Abbey Road Farm
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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
Hotel Elliott
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3.6
Hotel Elliott
A boutique hotel in downtown Astoria featuring a rooftop patio, historic charm, and beautifully appointed themed rooms.
3.6

Local Events & Happenings

The Black Keys
The Black Keys
The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
McMenamins Historic Edgefield Manor in Troutdale (8.51 mi)
28 May 2026
Visit Website
Sierra Ferrell
Sierra Ferrell
The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
McMenamins Historic Edgefield Manor in Troutdale (8.51 mi)
31 May 2026
Visit Website

Bob Dylan w/ Lucinda Williams
Bob Dylan w/ Lucinda Williams
The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
McMenamins Historic Edgefield Manor in Troutdale (8.51 mi)
5 Jun 2026
Visit Website
Rainbow Kitten Surprise w/ Spacey Jane
Rainbow Kitten Surprise w/ Spacey Jane
The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
McMenamins Historic Edgefield Manor in Troutdale (8.51 mi)
13 Jul 2026
Visit Website
Charley Crockett
Charley Crockett
The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
McMenamins Historic Edgefield Manor in Troutdale (8.51 mi)
15 Jul 2026
Visit Website
Bob Moses w/ Cannons
Bob Moses w/ Cannons
The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
McMenamins Historic Edgefield Manor in Troutdale (8.51 mi)
16 Jul 2026
Visit Website
Cake
Cake
The event will take place at McMenamins Historic Edgefield Manor in Troutdale.
McMenamins Historic Edgefield Manor in Troutdale (8.51 mi)
25 Jul 2026
Visit Website

Travel Gems from Reddit

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
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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
View on Reddit

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
View on Reddit
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
View on Reddit
Oregon 4-Day Itinerary: Gorge Mt. Hood Silver Falls Coast Portland Or Should I Reverse It? ... Stops between cannon beach and Portland.
Spent the weekend exploring Columbia River Gorge, Mt Hood and Cannon Beach
Oregon 4-Day Itinerary: Gorge Mt. Hood Silver Falls Coast Portland Or Should I Reverse It? ... Stops between cannon beach and Portland.
/r/Portland
View on Reddit
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
Oregon 4-Day Itinerary: Gorge Mt. Hood Silver Falls Coast Portland Or Should I Reverse It?
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
/r/oregon
View on Reddit
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 ...
Columbia River Gorge & Mt Hood day trip advice - what can we add or skip?
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 ...
/r/askportland
View on Reddit
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...
Advice for short Oregon trip I am making soon.
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...
/r/oregon
View on Reddit
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...
Places to visit & things to do in 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...
/r/oregon
View on Reddit
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 ...
First trip to Oregon - need help with itinerary
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 ...
/r/oregon
View on Reddit
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
Critique my Oregon Vacay Itinerary
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
/r/oregon
View on Reddit

7 Best Places For Weekend Trips From Gresham, OR

Weekend Getaway Itinerary Overview from Gresham, OR

Recommended Activities

Columbia River Gorge

Mount Hood

Hood River

Cannon Beach

Silver Falls State Park

Astoria

Bend

Restaurants

Multnomah Falls Lodge Restaurant

Multnomah Falls Lodge Restaurant

Rimrock Café at Timberline Lodge

Rimrock Café at Timberline Lodge

Solstice Wood Fire Pizza

Solstice Wood Fire Pizza

Stephanie Inn Dining Room

Stephanie Inn Dining Room

Bowpicker Fish & Chips

Bowpicker Fish & Chips

Hotels

Timberline Lodge

Timberline Lodge

McMenamins Edgefield

McMenamins Edgefield

Cannon Beach Hotel

Cannon Beach Hotel

The Silo Suites at Abbey Road Farm

The Silo Suites at Abbey Road Farm

Hotel Elliott

Hotel Elliott

Local Events & Happenings

The Black Keys

The Black Keys

Sierra Ferrell

Sierra Ferrell

Bob Dylan w/ Lucinda Williams

Bob Dylan w/ Lucinda Williams

Rainbow Kitten Surprise w/ Spacey Jane

Rainbow Kitten Surprise w/ Spacey Jane

Charley Crockett

Charley Crockett

Bob Moses w/ Cannons

Bob Moses w/ Cannons

Cake

Cake

Travel Gems from Reddit

In Gresham area for the weekend, what to do?

What is it like living in Gresham?

What are your favorite things past 82nd?

Where would you stay for a quick weekend trip?

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

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

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

Advice for short Oregon trip I am making soon.

Places to visit & things to do in Oregon..

First trip to Oregon - need help with itinerary

Critique my Oregon Vacay Itinerary