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. Central Oregon Escape .

The Full Story

SEPT. 29 - OCT. 1, 2023




Let's hit the road! Your trusty guides (pictured here) will meet the group at a designated spot at 10:00AM. Our first stop will be a quick detour to stretch our legs and get in a short little hike along the stunningly-blue Metolius River. We'll then grab lunch in the town of Sisters, and head out onto our first big hike: the Tam McArthur Rim Trail, a 5.3-mile out-and-back, moderate-rated trail with gorgeous valley views. Afterward, we'll continue on into Bend and get settled into our rental home. For dinner, we'll dine al fresco in famous Drake Park, and embark on a wine- or beer- (or both?) tasting journey from local famous producers. We will then sneak over to McMenamin's St. Francis School for a cocktail from their locals-only secret lounge. We'll end our day back at our rental home, soaking in the hot tub and gearing up for an early morning!

Meals Included: L,D



After a hearty home-cooked breakfast (featuring locally-made Sisters Coffee, of course) we'll head to world-famous Smith Rock State Park for a full day out on the trail. We'll hike the Misery Ridge & Summit Trail Loop, a 6.2-mile, hard-rated hike. As we travel we'll take in the absolutely stunning views of the valley and surrounding mountains rock formations like Monkey Face. We'll stop for lunch along the trail, and watch rock climbers rising and falling on the rocks all around us.

Upon returning back to our rental home, we'll take a much-deserved dip in the hot tub and nosh on a little charcuterie, then freshen up and head out for the evening. We'll enjoy a hearty dinner out at a local favorite hot spot, then hit one Bend favorite you won't want to miss: their old-school video game arcade - which also serves beer! After you've succeeded in beating your best scores at Centipede, ladies can either head back to the house or continue on to some popular hot spots* (that we highly recommend!).

Meals Included: B, L, D

*Not included


We head home today, but we're not done yet. After another hearty home-cooked breakfast and preparing the rental home to vacate, we will leave Bend and travel back north to Camp Sherman, where we'll embark on Koosah and Sahalie Falls Trail, a 2.4 mile moderate-rated loop trail that will take us to two waterfalls and give us up-close views of the wild McKenzie River. This easy, gorgeous hike will be the perfect way to stretch any sore muscles, and say farewell to beautiful Central Oregon as we head back to Portland to say goodbye!

Meals Included: B, Snack

Level of Difficulty: This is a Challenging tour for fit hikers who will find this a satisfying and challenging workout; not appropriate for unfit hikers.

Accommodations, double occupancy
All transportation
All activities & associated costs
All meals 
All gratuities

*Additional alcohol 

Limited to 8 participants.

Cost: $399 per person

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