Portland
Pearl District
Explore boutiques and galleries, and visit Powell's City of Books
Check out the food vendors in at Pine Street Market
Suggested restaurants: Ten Barrel Brewery, Wailua Shaved Ice, Screen Door, Multnomah Whiskey Library, (will take walk-ins but be sure to call), Papi Chulo’s, Ken’s Artisan Bakery, Salt & Straw Ice Cream
Northwest Portland 
Forest Park: Spanning over 5,000 acres, this expansive urban forest boasts more than 80 miles of trails. It's ideal for hiking, biking, and birdwatching.
Pittock Mansion: Perched in the West Hills, this historic mansion offers panoramic views of Portland and insights into the city's past. 
** Insider tip for hiking/ trail running - Park at Upper Macleay Trailhead and can head in either direction - short climb down to “Witches Castle” or up the trail to Pittock Mansion for portland views
Oregon Zoo
Rose Garden & Portland Japanese Garden
Northeast Alberta Arts District & Mississippi Street 
This area is known for its vibrant art scene, with murals, galleries, and vintage shops. 
Suggested Restaurants: Sports Bra, Cheese & Crack, Prost Brewery & Matt’s BBQ (nextdoor to one another), Han Oak, Eem Thai BBQ, Guero, Proud Mary Cafe, Terra Mae, Kaya
Central East Side & South East 
Ride the Portland Aerial Tram from the South Waterfront to the viewing platform at OHSU for great views
Suggested Restaurants: Kann, Scotch Lodge, Bible Club PDX, Gado Gado, Cheese & Crack, Basilisk, Wonderlove Food Truck Pod, Hawthorne Food Truck Pod
Food Carts
Check out the Portland Food Carts map to find delicious options: Food Cart Map
Around Portland 
Swan Island & Sauvie Island - September is peak Dahlia blooms at Swan Island
Check out the iconic Multnomah Falls and on the way back stop for lunch at Sugar Pine Drive In
Timberline Lodge - historic lodge on Mt Hood with great views. May run into snow on the mountain in September. Check the weather first. 
Trillium Lake - Base of Mt. Hood. Beautiful Lake loop. Check the weather first. 
Silver Falls State Park - Fall colors and many waterfalls 


Hood River & Columbia River Gorge
Columbia River Gorge Scenic Drive
Bordering Oregon and Washington, stretching 80 miles along the Columbia River. Highlights include waterfalls, scenic vistas, hiking trails, windsurfing, vineyards, breweries and historic towns. 
Hood River Fruit Loop  (Highly Recommend) - 35 mile scenic drive with big views of Mt. Hood & Mt. Adams with vineyards, orchards, and cider houses. September is peak apple picking season.
Stop at Panorama Point for views and photos
Bring a picnic to Mt. Orchard Views and pick apples with Mt. Hood in the background
Visit Stave and Stone Winery for great views of both Mt Hood and Mt Adams from the tasting room
Hiyu Wine Farm
Kiteboard/ Windsurfing: 
Watch or learn to Kiteboard on the Columbia River
Biking:
Bike the historic Columbia River Highway State trail. Bike rentals from Sol Ride.
Hiking: 
Dog Mountain Trail (hard), Eagle Creek (Out and back - can go as far as you want), Wahkeena & Multnomah Falls Loop
Willamette Valley (Wine Country) 
Winery Suggestions: (Highly Recommended)
Willamette Valley Vineyards Located just south of Salem, this expansive estate offers a variety of tasting experiences, including indoor and outdoor seating with panoramic vineyard views.
Resonance Winery Stunning tasting room, famous for Burgonday Style wines
Stangeland Vineyards & Winery A family-owned winery known for its small-lot Pinot Noir and Chardonnay, providing an intimate tasting experience.
Corollary Wines Specializing in sparkling wines, Corollary offers tastings by appointment, focusing on méthode champenoise techniques. 
Coeur de Terre Vineyard Situated in McMinnville, this vineyard emphasizes estate-grown Pinot Noir and sustainable farming practices.
Sealionne Wines A unique tasting experience featuring a 1971 Airstream trailer as its centerpiece, offering a relaxed atmosphere and diverse wine selections. 
Durant Vineyards Located in Dundee Hills atop Red Ridge Farms It is a family owned estate producing Pinot Noir, Chardonnay, and Pinot Gris. Most notably has a commercial olive mill and offers olive oil tastings. 
Sokol Blosser produces sustainable Pinot Noir, Chardonnay, and sparkling wine in scenic all organic vineyards. 
Late Sky Winery 
 Food Recommendations: Red Hills Market, Willamette Pie Co, Merenda Deli, Pinch, EZ Orchards Shortcake Stand, Rosmarino, Hayward, Territory
Accommodation recommendations: The Allison, Inn the Ground, The Grange Estate, Sosta House 
General Resource Guides: Willamette Wines, Eater Willamette - Wine, Eater Willamette - Food
Oregon Coast 
Cannon Beach: Haystack Rock (featured in the Goonies). Known for colorful tide pools and diverse birdlife. Watch out for the resident Elk herd! Stop by Bruce’s Candy Kitchen on your way out for some saltwater taffy and homemade fudge. One of our favorite coastal hikes in Cannon Beach is Ecola State Park.
Tillamook Cheese Factory: Guided tours, cheese tastings, and local ice cream. 
Pacific City: Cape Kiwanda State Park. Great views of the coast. Work up an appetite on the hike and visit Pelican Brewery for some good food and local beer.  
Manzanita: One of our favorite Oregon coastal spots - quaint and beautiful! Short Sands Beach - breathtaking cliff views. The Winery at Manzanita - wine tasting and cute rooftop that overlooks the water. Their logo is a dog - naturally one of our favorite spots. Oswald West State Park.  Another hike with breathtaking views of the coast line. Cape Falcon is a great hike in this park - can’t beat it! 


Within 4 Hour Drive
Seattle, WA
Mt. Rainier National Park, WA 
Bend, OR
Gig Harbor, WA
Crater Lake National Park, OR