Arrive at Redmond Municipal Airport or drive in from PDX, pick up your rental car, and head into Bend to drop bags at your hotel (consider a family-friendly option like Oxford Hotel Bend or a budget-friendly vacation rental near downtown). Take a short stroll along the Deschutes River Trail by Drake Park to stretch legs and get a feel for Bend’s sunny, high-desert air before grabbing a casual coffee and pastry at Lone Pine Coffee Roasters.
Check into your room and unpack, then walk to the High Desert Museum for an easy, kid-friendly introduction to the region’s wildlife, geology, and Native culture—plan on 1.5-2 hours to see live raptor demos and interactive exhibits. After the museum, explore downtown Bend’s lively third street: pop into independent shops, the Bend Ale Trail visitor center for brewery maps, and grab sandwiches or wood-fired pizza at Brother Jon's or Spork for a relaxed family lunch.
For dinner, head to a family-friendly brewpub such as Deschutes Brewery Public House where kids can enjoy mac & cheese while adults sample local IPAs and seasonal fare; alternative: the casual and tasty 10 Barrel Brewing Co. Walk off the meal with an easy riverside sunset stroll at Pilot Butte’s lower trailhead (if energy permits), then return to your hotel to rest up for tomorrow’s hike and museum day.
Wake up refreshed and head to the nearby Shevlin Park for an easy, family-friendly loop along the Tumalo Creek gondola trail—this 2-3 mile route offers gentle terrain, spring wildflowers, and a chance to spot waterfowl and river otters before crowds arrive. After the hike, refuel with hearty breakfast fare at Jackson's Corner or Sparrow Bakery downtown, where the kids can enjoy pancakes while you sip local coffee and plan the museum hop.
Spend the afternoon exploring Bend’s compact museum scene starting with the High Desert Museum if you want a deeper look (if you skipped exhibits on Day 1) or the Deschutes Historical Museum for local stories and rotating exhibits; both are interactive and great for kids. Follow up with a stroll through downtown’s Third Street to pop into the Cascades Raptor Center (check for special programs) or the Art on the Alley galleries, then grab a casual lunch at Spork or Worthy Brewing for family-friendly plates and outdoor seating when weather allows.
As the sun lowers, embark on a relaxed brewery crawl along the Bend Ale Trail—start at Deschutes Brewery Public House for classics, then sample sours at Crux Fermentation Project or unique seasonal brews at Boneyard Beer while older kids or adults enjoy tasting flights. Cap the night with a laid-back dinner at 10 Barrel Brewing Co. or Velvet, then return to the hotel for an early night—tomorrow’s full-day Smith Rock adventure will be an early drive and a big day.
Get an early start and drive the ~45 minutes from Bend to Smith Rock State Park so you can beat crowds and catch the golden morning light on the towering volcanic cliffs; park at the main lot and tackle the iconic Misery Ridge to Summit Loop for dramatic views of the Crooked River—bring layers, water, and sturdy shoes. Pause at the summit overlook for family photos and a snack, then descend toward the river for a gentler stretch along the River Trail where kids can hunt for interesting rocks and watch climbers on the cliff faces.
After working up an appetite, head into nearby Terrebonne for a leisurely lunch at The Cove Palisades Visitor Center picnic area or grab sandwiches and coffee from Smith Rock Café to eat amid the park’s picnic spots; rest up and let the kids run in open spaces. In the afternoon explore easier trails like the Canyon Trail or take a short interpretive walk to the Crittenden Bridge to learn about local geology and climbing history, or opt for a guided river or family-friendly climbing intro if you booked ahead with a local outfitter.
Return to Bend in time for a relaxed dinner—stop at Worthy Brewing for wood-fired pizzas and a family-friendly outdoor space, or try Ariana for approachable, seasonal Oregon fare if you prefer a sit-down meal. Finish the day with a low-key riverside stroll at Drake Park to unwind and compare favorite Smith Rock moments before turning in early; you’ll appreciate the rest after a full day of outdoor adventure.
Start the day with a leisurely, family-friendly stroll along the Lava Lands Visitor Center trails at Newberry National Volcanic Monument — the short, well-marked trails and dramatic lava flows are perfect for curious kids and offer interpretive signs that make geology fun. After exploring the visual wonders of lava fields and the Big Obsidian Flow overlook, stop at the visitor center for hands-on exhibits and a picnic-style snack while the kids compare their favorite volcanic finds.
Head back toward town for an engaging visit to the Oregon Observatory at Sunriver (seasonal; check hours) or the interactive exhibits at the High Desert Museum if you want a repeat-but-deeper experience focused on science and wildlife — both options offer live demonstrations and kid-friendly programming that build on the morning’s geology theme. If you pick the High Desert Museum, plan to catch a scheduled raptor program and let the children explore the living history area; afterward, grab an easy late lunch at the museum café or nearby Jackson's Corner in Bend.
For a relaxed evening, return to downtown Bend for a casual dinner at Bend Brewing Company or Worthy Brewing, where wood-fired pizzas and kid plates keep everyone happy while adults sample local brews. Finish with a sunset stroll along the Deschutes River Trail by Drake Park or a quick climb up Pilot Butte’s lower viewpoints for one last panoramic family photo before turning in and prepping for your final morning hike and brunch tomorrow.
Wake early for one last refresh: take the family on the Pilot Butte Summit Trail for a short but rewarding climb with 360° views of Bend, the Cascades, and Smith Rock in the distance — it’s an easy, camera-ready finale to your outdoor days and perfect for stretching before travel. Return to town and swing by Sparrow Bakery or Jackson's Corner for a hearty brunch (pancakes, breakfast sandwiches, or grain bowls) while you reminisce about favorite hikes and pack the car.
If your flight or drive schedule allows, spend a relaxed late morning browsing any final downtown shops on Third Street or pop into the Deschutes Historical Museum for a quick local-history stop to round out the trip; otherwise, take a peaceful riverside walk along the Deschutes River Trail by Drake Park to let the kids burn off energy before heading to the airport. Return your rental car at Redmond Municipal Airport with time to spare, grab a final coffee from Lone Pine Coffee Roasters if you need it, and prepare for departure feeling refreshed and full of Oregon memories.
Depending on travel timing, plan for a low-key dinner near the airport or at home — if you're still in Bend, pick up family-friendly takeout from Worthy Brewing or 10 Barrel Brewing Co. for the drive; if you’ve already landed back at PDX, enjoy a simple home-cooked meal and unwind while going through photos and highlights from your five-day adventure. Close the trip by noting a few must-return spots — Smith Rock, the High Desert Museum, and Bend’s brewery scene — to plan your next family getaway.