Crater Lake and Bend, OR

We start the trip in Portland, Oregon, a small city set along both sides of the Willamette River (pronounced Will-am-it). Portland is known for its strong coffee, friendly locals, and creative food scene. Summer is the best time of the year to visit!

Hop in a taxi at the airport and head to The Heathman Hotel. Your hotel is right in downtown Portland. (You can also take the MAX light rail train from the airport if you prefer).

Check into the hotel and explore the Rose City a bit before meeting up with the group. You can walk to Powell’s Books, the largest independent bookstore in the world or head up to the International Rose Test Garden and smell the blooms. There's lots to do!

Tonight, we will share dinner together at Higgens, one of the city’s most well-known and well-loved farm-to-table restaurants. Meet the other women on this journey and go over the plan for tomorrow’s departure with Regina, the trip leader.

We'll have breakfast at the hotel before we hit the road and head south for an introduction to Oregon vines and wines. We're on our way to the Willamette Valley, Oregon’s premiere wine-making region. We'll stop to sip and swirl at two vineyards and then enjoy lunch together.

From the vineyards, it’s a quick ride to McMinnville, a sweet little wine-country town where charm and boutiques abound.

We'll check into The Atticus Hotel, our designer digs for tonight, and then explore McMinnville with a GG2TW friend. McMinnville is full of fun restaurants and bars. Choose your favorite for dinner on your own tonight.

Enjoy breakfast at the hotel or head out to one of the many McMinnville cafes. Then we’re hitting the road and making our way southeast toward Bend.

On the way, we will stop at Silver Falls State Park, one of Oregon’s true gems. This verdant wonderland is littered with rushing waterfalls and babbling brooks set along the Trail of 10 Falls.

We'll enjoy a gentle walk to one of the falls and a picnic lunch in this magical place.

Now that we’ve had our dose of Oregon green, let’s move south to the high desert and our home for the next few nights, Bend.

We'll check into the fun and funky St. Francis Hotel in downtown Bend. The St. Francis is an Oregonian landmark. Set in a historic Catholic school from the 1930s, this is the right place to get an education on quirky Oregonian culture. Explore the grounds and St. Francis’ many bars, restaurants, and even a soaking pool. Like all McMenamin’s buildings, St. Francis has been decorated by local artists and tells us the story of those who enjoyed this space before us. 

Get settled in your King Room and then head out to see downtown Bend, a welcoming town on the banks of the Deschutes River.

Tonight, we'll enjoy dinner together at locavore spot, 900 Wall.

After breakfast at the hotel, you'll have some options on how to spend the day.

Option #1 - For the Adventure Seekers, we'll explore Newberry, the largest volcano in the Cascade Mountain Range, with a 21-mile base and a summit that is estimated to have once stood at 8,984 feet. The most recent Newberry eruption was just 1,300 years ago and formed the Big Obsidian Flow, a mountain of silicic rock that resembles broken glass shards. We'll explore the one-mile trail through the black flow and then drive to Paulina Peak for an expansive view and a photo op.

This trail has no more than 200 ft of elevation gain. We'll be walking on obsidian and rocky pathways and may want your walking poles. The trail is short, but we'll want to stop often to take photos of the lake and the giant boulders of obsidian all around you. 

Lunch lakeside following our hike in this black-glass wonderland.

We'll meet up as a full group for dinner tonight at The Pine Tavern right on the river in downtown Bend. Share stories from the day and enjoy some local Oregon wines.

For the Relaxation Seekers, instead of the Cascades, we’ll spend our morning getting a spa treatment in downtown Bend. Your massage is included in your GG2TW trip, but you can also add on more for a longer spa day, including wraps, facials, and mani/pedis. We can help you book all of this at Spa W.

After our spa time, we'll have lunch in downtown Bend. The rest of the day is yours to shop in local boutiques, rest, walk along the waterfront and get to know this charming town.

We'll meet up as a full group for dinner tonight at The Pine Tavern right on the river in downtown Bend. Share stories from the day and enjoy some local Oregon wines.

We're up early for breakfast then it’s time to hit the road to Crater Lake National Park, about 1 hour south of Bend. We'll travel south through the high desert to arrive at the park. Notice the juxtaposition of the lush western slopes we saw around Portland and the arid landscape in the central part of the state.

You may have seen Crater Lake's azure water held by the almost perfectly round caldera in photos. Now it’s time to see it in person. Crater Lake’s fresh water is some of the clearest found anywhere in the world.

Once in the park, we will break for numerous vistas, pop into the historic lodge, and partake in short walks. We'll also have time to explore a bit around the Visitor Center on our own and just take in the views.

We will not walk to the water’s edge (a very difficult trail that is straight down and straight up). None of our walks at the lake will be especially challenging or long. Expect lots of stops to get different angles of the lake and also short jaunts to viewpoints.

We'll enjoy lunch at Crater Lake National Park and relax in the summertime weather and the impressive landscape.

In the afternoon, we'll make our way back to Bend for some R&R at the hotel (and maybe a drink at their bar). Dinner's on your own tonight - you may want something casual in town ... or room service!

After breakfast, we'll make our way north toward Portland, pausing at some of Oregon’s most impressive sites along the way. 

We'll make our way across the Warm Springs Reservation and take in the scenery. Oregon is a beautiful and varied state with epic vistas that are sure to impress.

As we cruise further north, we'll stop at jagged Smith Rock State Park. Known as one of the 7 Wonders of Oregon, Smith Rock is where outdoor enthusiasts come to hike, bike, and connect with nature.

Cliffs of tuff and basalt make for ideal rock climbing, but we won’t be doing any difficult hikes. Instead, take in the view from a short, flat rim trail (less than1 mile) and see if you can spot golden eagles, prairie falcons, river otters, or beavers.

Our next stop is an active volcano and a guided tour of historic Timberline Lodge set atop Mount Hood, a popular skiing and hiking destination. Learn more about this impressive retreat built in 1937.

After exploring, we’ll meet for lunch together at the Cascade Dining Room inside the historic lodge.

Then it’s time for a ride on the Magic Mile Chair Lift to the mountain’s 7000′ level – no skis or snowboards needed! The spectacular view of Mt. Hood, Palmer Snowfield and nearby Mt. Jefferson is one you’ll never forget. If you’d rather skip it, hang back at the lodge and enjoy a cup of coffee or a glass of wine.

In the late afternoon we will arrive in Portland.

Freshen up and rest a bit be Papa Haydn, a city favorite known for their fresh northwestern dishes and outrageous cakes.

Let’s toast to a great summer adventure and new connections made.

Today we must say adieu, but our memories and new friends made will last a lifetime.

Extend your stay and see more of Oregon or head to the airport today to fly home. Stay in touch with your new GG2TW friends via Whatsapp to plan future getaways.