Bend, Oregon Bachelor Party Itinerary

Day 1: Arrival & Downtown Fun

Morning: Fly into Redmond Regional Airport and take a short shuttle to your downtown Bend hotel. Drop off luggage and enjoy a quick coffee at Thump Coffee while soaking in the mountain vibe.

Afternoon: Stroll along the Old Mill District, checking out boutique shops and the scenic Deschutes River Trail. Grab a bite at 10 Barrel Brewing Co. for some local craft beer and hearty pub fare.

Evening: Kick off the celebration with a private dinner at Wild Rose, featuring upscale Pacific Northwest cuisine. Afterwards, hit the bars on Wall Street, starting with Deschutes Brewery for a lively taproom atmosphere.

Day 2: Outdoor Adventure & Nightlife

Morning: Fuel up with breakfast at Bakeries and head out for a guided white‑water rafting trip on the Deschutes River, perfect for adrenaline‑seeking groups.

Afternoon: After lunch, tackle the iconic Smith Rock State Park for a half‑day hike and rock‑climbing session, offering stunning red rock vistas and photo ops.

Evening: Return to Bend for a relaxed dinner at Crux Fermentation Project. Continue the party at The Loose Goose, a lively spot known for its DJ nights and dancing.

Day 3: Relaxation & Farewell

Morning: Recover with a leisurely brunch at The Victorian, then soak in the natural hot springs at McMenamins Old Mill for a soothing start.

Afternoon: Explore the High Desert Museum for a quick cultural fix, followed by a casual bike ride along the Deschutes River Trail to enjoy the scenery.

Evening: End the trip with a farewell dinner at Portland Trail Lodge, featuring a private grill and a toast to the groom. Wrap up with a nightcap at Bend Alehouse before heading back to the hotel.

Time and Cost Estimates

• Thump Coffee – 30 min – $10 per person
• 10 Barrel Brewing Co. – 1 hr – $15 per person
• Wild Rose – 2 hr – $60 per person
• Deschutes Brewery – 2 hr – $25 per person
• White‑water rafting (Deschutes River) – 4 hr – $120 per person
• Smith Rock State Park (hike & climb) – 5 hr – $20 per person (parking & gear)
• Crux Fermentation Project – 2 hr – $30 per person
• The Loose Goose – 3 hr – $20 per person
• The Victorian (brunch) – 1.5 hr – $25 per person
• McMenamins Old Mill (hot springs) – 2 hr – $15 per person
• High Desert Museum – 2 hr – $18 per person
• Portland Trail Lodge (private dinner) – 2 hr – $80 per person
• Bend Alehouse – 1 hr – $15 per person
• Total Estimated Cost – $453 per person

Tips

To extend the trip, add an extra day for a full‑day mountain bike excursion at Mt. Bachelor or a day‑trip to Newberry National Volcanic Monument. If you need to shorten the itinerary, skip the afternoon hike at Smith Rock and replace it with a relaxing spa session at Sunriver Resort, keeping the core activities—river rafting and nightlife—intact.