Weekend Travel Ideas

Music Lover Weekend

For the visitor coming from Portland, Seattle, or Eugene who's here for the show first and everything else second.

  • 4:00 PM — Check into the Waypoint Hotel. You are already at Midtown in Bend. Drop your bags, walk the block.

    Thirsty? Hungry?

    Stop by Midtown Yacht Club and enjoy a cold beer and great food cart snacks for a reasonable price.  You’ll find good people and no hassle with a relaxed vibe.  Here is walking directions.

    8:00 PM — Opening Night Song of Sunset: Cosmic Heirloom Speakeasy - Friday Oct. 23, 2026 - 6pm - 9 PM at WayPoint Hotel. Limited seating - GET TICKETS

    10:00 PM - Looking for a true Bend dive bar experience? M & J Tavern delivers local character, cold drinks, and a glimpse into the community spaces that help keep Central Oregon's music and storytelling culture alive. Featured in Song of Sunset: The Living Room, it's a stop worth adding to your Bend weekend itinerary.

  • 8:30 AM — Coffee at Thump Coffee on NW Newport Ave. They roast in-house. Get the single-origin pour over and sit down for 20 minutes before the day starts. Budget $6–9.

    10:00 AM — Walk the Old Mill District along the Deschutes River. Free, easy, about an hour. Good record shops and bookstores if you want to browse. Pick up something local.

    12:30 PM — Lunch at Spork on NW Galveston Ave. Global street food, fast and affordable, popular with locals. Budget $14–18 per person.

    2:00 PM — Rest, nap, read. This is intentional. The show runs late and you want energy for it.

    5:30 PM — Early dinner or snacks at Deschutes Brewery Public House on NW Bond St. River views, great food, and you can sample the lineup before the evening. Budget $18–28 per person. Show your event badge for a complimentary pint (sponsor offer).

    7:00 PM — Song of Sunset: Underground. Doors at 6:30. The main live music showcase — featured Pacific Northwest artists, intimate venue, late set runs until approximately 11 PM.

  • 9:30 AM — Brunch at McKay Cottage on NE Butler Market Rd. Cash-only, long-standing Bend classic, worth the wait. Budget $14–22 per person.

    11:00 AM — Sunday Acoustic Showcase. Included with your weekend pass. Short sets, artist meet-and-greet, community closing. Ends by 1 PM.

    1:00 PM — Drive home. Stop at Strictly Organic Coffee in Redmond if you're heading north, or grab a Lone Pine Coffee on your way out of town.

Adventure + Music Weekend

For the visitor who wants to earn the evening. Trails and rivers by day, stages by night.

  • 3:00 PM — Leave Portland or Eugene by noon, Eugene by 1 PM. Bend is 3 hours from Portland, 2 hours from Eugene on clear roads.

    4:00 PM — Check into the Waypoint Hotel. Change clothes. The hotel has secure bike and gear storage if you're bringing equipment.

    5:00 PM — Dinner at Worthy Brewing on NE Steele Rd. Large outdoor space, solid pub menu, easy energy for a Friday arrival. Budget $20–32 per person.

    8:00 PM — Opening Night Song of Sunset: Cosmic Heirloom Speakeasy - Friday Oct. 23, 2026 - 6pm - 9 PM at WayPoint Hotel. Limited seating - GET TICKETS

  • 7:00 AM — Sunrise at Pilot Butte State Scenic Viewpoint. It's a cinder cone right inside Bend city limits. The hike to the summit takes about 20 minutes and puts the entire Cascade Range in front of you. Free. Bring coffee from the hotel lobby.

    9:00 AM — Breakfast at Victorian Café on NW Riverside Blvd. A Bend institution. Expect a short wait on weekends. Budget $12–18 per person.

    10:30 AM — Rent kayaks or paddleboards from Tumalo Creek Kayak & Canoe. A two-hour float on the Deschutes is calm enough for beginners and beautiful enough to slow anyone down. Show your event ticket for $10 off your rental. Budget $35–55 per person after discount.

    1:00 PM — Post-float lunch at Crux Fermentation Project on SW OSU Way. Outdoor patio overlooking the Deschutes, experimental ales, wood-fired food. Budget $18–26 per person.

    3:00 PM — Optional: drive 25 minutes to Smith Rock State Park if you want more. The Misery Ridge Loop is 3.9 miles and takes about 2 hours. Or rest — the show is tonight.

    6:00 PM — Back to the hotel. Clean up. This is the payoff evening.

    7:30 PM — Early arrival for Song of Sunset: Underground. Doors at 6:30. Being early means better position for the headline set. This is what the whole day was building toward.

  • 7:30 AM — Phil's Trail Network off Skyliner Road. One of the best mountain biking and trail running systems in the Pacific Northwest. Go for an hour or two depending on fitness. Free, well-marked, all-abilities sections available.

    10:30 AM — Coffee and recovery food at Lone Pine Coffee Roasters on NW Franklin Ave. Excellent espresso drinks and breakfast sandwiches. Budget $8–14 per person.

    1:30 PM — Drive home via the McKenzie Pass Scenic Byway (Highway 242) if it's open and weather permits. One of the most dramatic drives in Oregon. Adds about 45 minutes but worth every one.

Couples Getaway Weekend

For two people who want cultural experience, good food, and a reason to stay an extra night.

  • 3:00 PM — Check in early at the Waypoint Hotel. Hossmer bar opens at 4 PM — start there before you do anything else.

    5:00 PM — Dinner at Deschutes Brewery Public House

    A Bend institution and one of Oregon's most celebrated craft breweries. Enjoy Northwest-inspired pub fare, award-winning beers, and a lively atmosphere in the heart of downtown. It's the perfect place to settle in after a day of exploring and before the evening's music and storytelling. No reservations required for most visits. Budget $40–70 per couple.

    7:00 PM — Opening Night Song of Sunset: Cosmic Heirloom Speakeasy - Friday Oct. 23, 2026 - 6pm - 9 PM at WayPoint Hotel. Limited seating - GET TICKETS

  • 9:00 AM — Breakfast in bed or a slow start at the hotel. No alarm.

    10:30 AM — Walk the downtown Bend art gallery circuit. Start at the Old Stone Church on NW Congress St and work your way toward Wall Street. Most galleries are free and open Saturday mornings. About 90 minutes if you linger.

    12:30 PM — Lunch at Spork One of Bend's most beloved local eateries, Spork serves globally inspired street food in a casual, creative atmosphere. It's the perfect midday stop after exploring downtown or the Old Mill District, offering bold flavors, local ingredients, and plenty of Central Oregon character. Budget $25–45 per couple.

    2:30 PM — Drive 30 minutes to Tumalo Falls on Tumalo Creek Rd. A 97-foot waterfall accessible by a short flat walk. Bring a blanket if you want to sit. Free with Oregon State Parks pass or $5 day-use fee.

    5:00 PM — Back to the hotel to change for the evening.

    6:00 PM — Song of Sunset: Underground. Doors at 6:00 — arrive early for a good spot together.

  • 10:00 AM — Brunch at Jackson's Corner on NW Brooks St. Community table feel, excellent breakfast bowls and pastries, Bend at its most local. Budget $22–36 per couple.

    12:00 PM — Sunday Acoustic Showcase. Included with pass. Shorter and quieter than Saturday night — good music for a Sunday morning mood.

    2:00 PM — Afternoon at the Old Mill District home of Hayden Home Amphitheater along the river if weather is good, or browse the shops on NW Wall Street. The Roundabout Books independent bookstore on NW Galveston is worth an hour.

    4:00 PM — Check out and head home, or stay a third night if Bend has done its job.