Planning a long weekend in the Columbia River Gorge? We’ve got the perfect Hood River & The Dalles weekend itinerary. Our 3-day itinerary is in-depth, with plenty of options including wineries, breweries, farmers markets, hikes, shops, and where to stay.
I’ve traveled all over the world, and to me, the Columbia River Gorge is still on of the most beautiful, magnificent places on Earth.
Picture this: a dramatic, river-carved canyon with waterfalls tumbling straight into the highway shoulder.
Now add orchards climbing the hillsides. Wind and kite surfers carving up the water below. And small towns that still feel like special discoveries instead of tourist destinations.
That’s the Columbia River Gorge, and it’s truly one of the most underrated weekend trips in the Pacific Northwest.
Just about 90 minutes from Portland, Oregon, you get basalt cliffs, world-class wine, and small-town charm without the crowds you’d find in wine country closer to the city.
Hood River and The Dalles anchor the eastern half of the Gorge. Together, they make the perfect two-town itinerary.
Hood River brings the postcard views, the lavender farms, and the fruit stands. The Dalles brings the history, the murals, and a wine scene that’s finally getting the attention it deserves.
Spend a 3-day weekend bouncing between the two, and you’ll leave with a phone full of photos, a trunk full of wine, and a real case for why this stretch of the Gorge deserves a spot on your travel list.
Table of Contents
- ⛰️ About Hood River and The Dalles
- The vibe
- Getting there from PDX
- 🗺️ Weekend itinerary for Hood River and The Dalles
- 🍷Wine tasting in the Columbia River Gorge
- Best wineries near Hood River
- 🍷 Best wineries near The Dalles
- Sunshine Mill Winery
- 🍽️ Where to eat in Hood River
- 🍽️ Where to eat in The Dalles
- Bargeway Pub
- Shannon’s Ice Cream
- The Coffee Shop
- 🌲 Hiking, biking, and taking in the sights in the Columbia River Gorge
- Rowena Crest Viewpoint Tip
- 🏞️ What to do in The Dalles
- 🌊 What to do in Hood River
- 🏨 Where to stay in The Dalles: Rayland Hotel
- Columbia River Gorge FAQs
- Book your next trip to the Pacific Northwest
- More Pacific Northwest travel articles
⛰️ About Hood River and The Dalles
The Columbia River Gorge has been a crossroads for thousands of years.
Native Americans, including the Wasco and Wishram tribes, fished and traded along this stretch of the river long before settlers arrived. The Dalles sat at a critical point on the Oregon Trail, where pioneers had to make a hard choice: raft the treacherous Columbia rapids or take the punishing Barlow Road around Mount Hood. That decision point shaped the town, and you can still feel that pioneer history in its historic downtown.
Hood River, meanwhile, grew up around orchards. Its mild microclimate turned it into one of the country’s top producers of pears, cherries, and apples, an agricultural legacy that eventually opened the door to the vineyards now dotting the hillsides.
The vibe
Hood River feels like an outdoor athlete’s dream, with a wine glass in hand. It’s the kind of town where someone in athletic wear orders a beer flight or flight of Pinot Noir right after a windsurfing session or a morning hike, and nobody blinks.
The Dalles, on the other hand, has a quieter, more historic energy. Think small-town main streets, century-old buildings, and a slower pace that makes it easy to actually relax.
Together, they give you both sides of the Hood Gorge experience: outdoor adrenaline and orchards on one end, history and quiet hidden-gem spots on the other.
Getting there from PDX
Getting to the Columbia River Gorge area from Portland International Airport is refreshingly simple. By car, head east on I-84, which hugs the Columbia River the entire way.
Hood River is about an hour from the airport, and The Dalles is roughly 90 minutes.
The drive itself is part of the experience. It’s truly one of the most picturesque, scenic drives in the United States, with waterfalls, cliffs, and river views the whole way. So be sure to budget extra time for photo stops!
There’s no reliable public transit option for this route, so a car is essential.
Why You Need to Visit the Columbia River Gorge
- Real small-town character, without the tourist markup.
- Two distinct towns, one easy road trip, no long transfers required.
- Wine tasting rooms tucked into an old flour mill, a converted barn, and orchard-view patios.
- The Fruit Loop puts fresh cherries, pears, and lavender within arm’s reach.
- Downtown murals turn a walk through The Dalles into a history lesson.
- Windsurfing, hiking, and biking all within minutes of your hotel.
- A genuinely walkable, historic downtown in both Hood River and The Dalles.
🗺️ Weekend itinerary for Hood River and The Dalles
Alain and I recently visited the Hood Gorge area for a long weekend. Here’s the general itinerary outline that we actually followed. It packs a LOT into a few short days, and gives you some of the best of the Gorge.
Add these stops to your itinerary for a fun weekend in the Columbia River Gorge!
Day 1
- Arrive around noon. Enjoy lunch and a wine tasting at Sunshine Mills Winery.
- Drive to the Rowena Crest Viewpoint and soak up the gorgeous Columbia River Gorge views.
- Check into the Rayland Hotel.
- Cool off with ice cream at Shannon’s Ice Cream.
- Shop at Oregon’s oldest bookstore, Klindt’s Books.
- Dine at the Hi-Way House.
- Check out the Wines on 2nd on your back to Rayland Hotel.
Day 2
- Breakfast at Rayland Hotel’s Caesura Cafe.
- Wander The Dalles Farmers Market (Saturdays).
- Enjoy lunch and a wine tasting at Annalemma Winery.
- Then move onto a wine tasting at Idiot’s Grace.
- Explore The Murals of The Dalles.
- Dinner and live music at Bargeway Pub.
Day 3
- Breakfast at The Coffee Shop.
- Check out of the Rayland Hotel.
- Walk the Riverfront Park Trail.
- Wine tasting at Marchesi Vineyards.
- Lunch and wine tasting at Stave and Stone Winery.
🍷Wine tasting in the Columbia River Gorge
Oregon’s Columbia River Gorge sits in the Colombia River AVA. This is where warm days, cool nights, and volcanic soils produce a diverse portfolio of wines. Whereas the Willamette Valley is known for Pinot Noirs and Chardonnays, here you’ll find more big red wines and crisp white wines
Best wineries near Hood River
Several wineries in Hood River are part of the scenic 35-mile Fruit Loop. This drive connects family-run orchards, farm stands, and a few surprise wineries. Depending on the season, you’ll find cherries, pears, apples, and pumpkins straight from the source.
Marchesi Vineyards
Marchesi Vineyard channels old-world Italian winemaking traditions in the middle of Oregon apple and pear country.
The Marchesi family’s Italian roots come through in both the wine list and the warm, unhurried hospitality. The winery produces Northern Italian varietals rarely found in Oregon, including Barbera, Dolcetto, Nebbiolo, Pinot Grigio, and Pinot Nero.
Instead of one large open wine tasting room, Marchesi offers several different types of seating. Most offer a bit of semi-privacy, making the tasting experience here more intimate and personal.
3955 Belmont Drive
Hood River, OR, US, 97031
For more information or to book your wine tasting, visit the Marchesi Vineyards website.
Stave and Stone Vineyards
Sitting outside on Stave & Stone Winery‘s patio, you are treated to one of the best wine tasting views around.
This boutique winery in Hood River is known for Rhône and Bordeaux varietals, along with Pinot Noir and Chardonnay. It’s an easy, unfussy stop to add to your loop.
My tip: order the Legacy Tasting, which includes five wines that are each paired with small bites. They do have a full food menu at Stave and Stone, too, so this is a great spot for lunch while wine tasting.
3827 Fletcher Drive
Hood River, OR, US, 97031
For more information or to book your wine tasting, visit the Stave and Stone website.
Phelps Creek Vineyards
A third wine tasting stop we recommend if you have time is Phelps Creek Vineyards. This beautiful site features estate-grown pinot noir and pinot gris that show off the region’s cooler-climate character. You’ll also enjoy beautiful mountain views here, and their wines are truly delicious.
🍷 Best wineries near The Dalles
Venture a little further east for wine tasting, and you’ll find wines that offer an even wider variety of expressions of the land. We’re talking more big reds like Cabernet Sauvignon and Syrah, and more crisp whites like Sauvignon Blanc and Albariño.
Analemma Wines
One of our favorite stops along the Gorge is Analemma Wines. Here you get it all: gorgeous, small production, biodynamic wines, sweeping scenic views, and one of the best food programs we’ve encountered at a winery.
Tucked among orchards and lavender fields with cliffs rising behind, Analemma produces a wide range of wines, from Albariño and sparkling wines to classic Oregon Pinot Noirs, to bold reds such as Cabernet Sauvignon, Syrah, and Grenache.
But foodies will adore their full food menu offered here. We’re talking sweet/salty vegan wine biscuits (pair it with their sparkling or one of the white wines). Amazingly fresh salads made with produce from their farm and neighboring local farms. Rich, hearty pastas made in house. Alain and I were blown away by the food here, as well as the wine. It’s probably one of our favorite places to go wine tasting in Oregon!
1120 State Road
Mosier, OR, US, 97040
For more information or to book a wine tasting reservation, visit the Analemma Wines website.
Idiot’s Grace Wines
Idiot’s Grace, also in Mosier, leans into old-world winemaking on a historic homestead property.
Here you can expect a rustic, unpretentious tasting experience surrounded by orchards and vineyard rows. It’s the kind of laid-back stop that feels more like visiting a friend’s farm than a formal tasting room.
This family-owned organic winery makes a lovely Chenin Blanc and Cabernet Franc. During our visit, we also tasted their Sauvignon Blanc, Millot, Dolcetto, and Syrah/Grenache.
8450 U.S. 30
Mosier, OR, US, 97040
For more information or to book a wine tasting, visit the Idiot’s Grace website.
Sunshine Mill Winery
Located right off the highway as you enter Mosier, you’ll find Sunshine Mill Winery. You can’t miss it with its imposing structure and large mural welcoming you into The Dalles.
Sunshine Mill Winery might be the most memorable tasting room in the entire Gorge. It’s so vibrant and colorful — I could spend all day here!
It’s housed inside an old flour mill that’s been standing for more than 130 years, complete with the original machinery and exposed brick. You can even see the old Thomas Edison motor that once powered it; the first electricity in The Dalles.
Sip on a flight of their wines on the sunny patio or in one of the many options for seating throughout the large, colorful, whimsical indoor space. Shop the local Oregon goods inside, or wander the on-site history museum before you go.
In addition to wine tasting, Sunshine Mill Winery also offers a full menu, so it’s a fun spot for lunch or dinner and wine tasting.
To learn more or to book your wine tasting experience, visit the Sunshine Mill Winery website.
🍽️ Where to eat in Hood River
During our recent visit, we didn’t have time to enjoy a full meal in Hood River. However, here are some places we’ve enjoyed on past visits.
Pfriem Family Brewers sits right on the waterfront, and it’s the kind of brewery that takes its kitchen just as seriously as its taps. The vibe is casual and lively, with an outdoor patio looking out toward the river and a European-leaning menu that goes well beyond standard pub fare. Order a flight alongside the schnitzel or the mac and cheese and settle in.
Solstice Wood Fire Cafe & Bar is where to go for pizza with real char. An imported Italian wood-fired oven turns out rustic pies made from slow-fermented, regionally milled dough, and the seasonal toppings lean hard into the Gorge’s orchards. The waterfront patio and sunroom make it an easy stop before or after a walk through the park across the street.
Ixtapa is the go-to for a casual, family-friendly Mexican meal. We’ve enjoyed food from Ixtapa Express taqueria food truck near the waterfront. Expect generous portions.
Celilo is the date-night pick. This farm-to-table restaurant in the heart of downtown has spent decades building relationships with local farmers and foragers, and the menu shifts with whatever’s in season, from house-made pasta to Pacific Northwest seafood. Expect a warm, art-filled dining room and a wine list built to match.
Broder Øst is the Scandinavian breakfast and brunch spot locals swear by. Think Danish pancakes, Swedish hash, and Nordic-style breakfast boards, all served in a cozy café inside the historic Hood River Hotel. It’s the right call for a slow morning before a day of wine tasting. Learn more at our Broder Øst article.
Gorge White House is less a restaurant and more a full afternoon out. Set on a working orchard with Mount Hood views, this historic farmhouse pairs a food cart serving flatbreads and burgers with a tasting room pouring hard cider and craft wine. Wander the u-pick fruit and flower fields while you wait for your order. Learn more at our The Gorge White House article.
🍽️ Where to eat in The Dalles
In addition to the Sunshine Mill Winery mentioned above, there are several spots to dine in The Dalles.
Hi-Way House
Don’t be fooled by the unassuming roadside exterior. The Hi-Way House is a classic diner stop that is full of delicious surprises.
For 80 years, the Hi-Way House has been a cherished landmark along historic US Highway 30 in The Dalles. With its iconic red booths and nostalgic black and white photos adorning the walls, you can witness the diner’s history while enjoying a menu that delivers big flavors.
Ask locals what’s the best dish here, and you’ll get dozens of different answers because each dish is cooked with care and thought. On our recent visit, we loved the mushroom ravioli, salmon special, taquitos, and steak bites. The service is spectacular, and they’ve got a great cocktail program.
2434 E 2nd St
The Dalles, OR 97058
Bargeway Pub
For riverside dining with a lively atmosphere, check out the Bargeway Pub. It’s THE outdoor spot for an easy, unpretentious dinner with a drink in hand. And they have live music almost every night.
Think classic pub fare, like the fish and tots and nachos pictured above, burgers, and sandwiches. The spacious restaurant welcomes a laid-back crowd for casual pub dining. Perfect for winding down after a day of exploring.
1535 Bargeway Rd
The Dalles, OR 97058
For more information, visit the Bargeway Pub website.
Shannon’s Ice Cream
Shannon’s Ice Cream is the essential downtown The Dalles stop. It’s a longtime local favorite for a reason!
This cute ice cream shop is in a charming craftsman home, not too far off the main street in downtown. Perfect spot to grab a scoop for a refreshing cool down on a warm summer day.
I love how they have several different dairy-free and vegan flavors!
Visit Shannon’s Ice Cream on Instagram for the latest.
The Coffee Shop
The Coffee Shop is where to fuel up before hitting the road. A solid espresso and a quiet corner to plan out the day’s wine tasting route makes it an easy first stop of the morning.
The Coffee Shop is colorful, quirky, and super fun. Plus it’s located in the Shops on 2nd building which houses four women-owned businesses. If you stop by after 10am, you can shop The Workshop, which is full of beautiful home goods, stationery, art, gifts, and more, many of them made by Oregon artisans.
🌲 Hiking, biking, and taking in the sights in the Columbia River Gorge
There are so many opportunities for hiking, biking, and walking in the Columbia River Gorge.
For waterfall hikes, you could do the popular Multnomah Falls hike. Or, my favorite family-friendly hike is the one at La Tourell Falls Loop.
I’ve biked the Historic Columbia River Gorge Highway Trail before between Hood River and Mosier. This section is a car-free 4.5 mile trail that’s a great place for families to ride together safely. The views are stunning!
The Dalles Riverfront Trail is a paved path along the Columbia that’s ideal for an easy hike or a bike ride. It has river views the entire way and a good stretch of shade for hot summer afternoons. The trail also connects to The Dalles parks, a marina, and waterfront recreation, while showcasing the area’s mix of natural beauty and industrial river history.
Between the two towns, pull off at Rowena Crest Viewpoint, one of the most photographed spots in the entire Gorge.
Perched high above the Historic Columbia River Highway, the overlook frames the famous switchback loops built into the cliffside back in the early 1900s, along with sweeping views east toward The Dalles and down over the Tom McCall Nature Preserve.
It’s an easy five-minute stop for photos. But you can also extend it into a short hike. The mile-long plateau trail wanders across the bluff to the cliff’s edge, while the steeper McCall Point trail climbs higher for an even bigger payoff.
Marlynn’s Tip
Rowena Crest Viewpoint Tip
Spring is peak season here, when wildflowers blanket the hillsides. It’s simply stunning! But, the view holds up any time of year. Just remember that this spot is VERY WINDY. You should exercise extreme caution when taking photos here. Our photos and videos make it look like I am sitting on the edge, but I’m actually not. I’m in a safe spot, and only ventured out onto this spot when the winds died down a bit.
🏞️ What to do in The Dalles
There is so much more to do in The Dalles besides just outdoor adventures, wine tasting, and eating! Take a stroll through historic downtown and discover colorful murals, beautifully preserved architecture, local shops, and the community’s rich history along the Columbia River.
Explore the Murals of The Dalles
If you love city murals as much as I do, you will love following the map of the Murals of The Dalles. This downtown public art collection includes dozens of large-scale paintings depicting Native American history, the Lewis and Clark expedition, and the pioneers who passed through on the Oregon Trail. Many are paired with printed legends so you can actually learn the story behind each one as you walk.
Klindt’s Booksellers & Stationers
Pop into Oregon’s oldest bookstore, Klindt’s Booksellers and Stationers. This cute shop has been serving readers since 1870. As a book lover, I could spend a good amount of time here. They have a good selection of current titles as well as books about Pacific Northwest history, outdoor adventures, and a fun cookbook section.
🌊 What to do in Hood River
As mentioned earlier, Hood River is truly the outdoor adventure lover’s playground. But even if you don’t windsurf or hike, there is so much to do here!
Hood River Lavender Farms is always a must visit stop for my family when we’re in Hood River. The lavender fields are almost picture perfect, with Mount Hood shining in the background. And the aroma of lavender surrounding you here is purely intoxicating. I love this spot!
Since 2003, this picturesque farm produces a wide variety of lavender products, from essential oils to soaps to food products. So definitely be sure to stop by the gift shop and the soft serve window while you are here snapping some photos.
Hood River Lavender Farms
3823 Fletcher Drive, Hood River, OR, US, 97031
For more information, visit the Hood River Lavender Farms website
Another stop along the Fruit Loop that I highly recommend: Kiyokawa Orchards.
🏨 Where to stay in The Dalles: Rayland Hotel
The Rayland is a new boutique property that sits right in the historic district of The Dalles. It’s down the street from Sunshine Mill Winery and a short walk to the downtown murals.
We stayed here during our recent trip and really enjoyed it. The rooms are clean, comfortable, and modern. We had a river view, and loved waking up to the sun rising over the Gorge each morning.
The on-site coffeehouse, Caesura Coffee, was a nice easy spot to grab coffee and a breakfast sandwich or pastry before heading out for a day of adventures.
Also check out our full article about our stay at the R & R Guest House in The Dalles.
Columbia River Gorge FAQs
Yes. Both Hood River and The Dalles are small, walkable towns with low crime rates and a steady flow of tourists, so solo travelers generally feel comfortable exploring on foot, especially during daylight hours.
Late spring through early fall (May through September) is the sweet spot, with warm days, blooming lavender, and ripe fruit at the Fruit Loop stands. Fall brings apple and pear harvest season and fewer crowds, while summer is peak windsurfing season in Hood River.
Yes. There’s no reliable public transit connecting Portland to the Gorge or linking Hood River and The Dalles, so renting a car at PDX is essential.
Yes, especially the Fruit Loop, lavender farms, and riverfront trail. Even wineries in Oregon tend to be family-friendly; just be sure to check each winery’s website before heading there.
Layers are key, since Gorge weather can shift quickly between the river and higher elevations. Bring comfortable walking shoes for the murals and riverfront trail, and for biking or hiking. Pack a light jacket for cooler mornings and for anytime you’re by the river (it gets really windy!!). And don’t forget sunscreen, since the sun reflecting off the river and basalt cliffs is stronger than you’d expect.
Book your next trip to the Pacific Northwest
Ready to visit Hood River and The Dalles in the beautiful Columbia River Gorge?
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Parts of this article were written based on our experiences during a hosted trip by Hood Gorge and Explore The Dalles. As always, all photos/videos and all opinions are our own.
