Bend, Oregon shines in summer and fall, with clear skies, high-desert trails, and a calendar packed with events that draw groups from all over the Northwest. Whether you’re planning a milestone birthday, a family reunion, or a getaway with friends, Bend offers the perfect backdrop: paddle board sessions on the Deschutes, afternoons at food cart pods, and unforgettable evenings under pink-orange sunsets. This guide will help you map out the best warm-weather activities for groups, local events worth timing your trip around, and what to look for when booking a large vacation rental that can fit your whole crew comfortably.
The Deschutes River offers everything from peaceful tubing to high-energy whitewater rafting. Popular with groups, the Big Eddy Thriller provides plenty of splash-worthy fun, while Mirror Pond offers a scenic six-mile float through downtown. Fly-fishing guides cater to beginners with on-site casting lessons before heading to top fishing spots. After a day on the water, unwind with a riverside picnic and watch the sunset light up Pilot Butte.
Solo paddlers find peaceful stretches for meditation between riffles, while couples enjoy tandem floats with frequent stops to dip their toes in. Early mornings offer calm water and misty views, ideal for quiet reflection or nature photography. Rentals and outfitters cater to all skill levels, making it easy to craft a custom day on the water.
Fifteen minutes from downtown, Tumalo frames an oxbow bend in the Deschutes beneath towering ponderosas. Reserve a riverside picnic shelter for your reunion barbecue, then let younger kids wade in the calm eddy while teens test their balance on stand‑up paddleboards. A level, stroller‑friendly path parallels the river for 2.4 miles, dotted with osprey nests and fishing pull‑outs. Evening light slants through red‑barked trunks, turning the swim beach into a golden amphitheater, bring camp chairs and a guitar for instant summer‑camp nostalgia.
Ringed by 1.6 million acres of protected land, Bend is trailhead central. Split the group by ambition: send summit‑chasers up South Sister while young families opt for Todd Lake’s wildflower stroll and photographers chase sunrise at Sparks Lake. Many trailheads sit off the Cascade Lakes Scenic Byway, so it’s easy to regroup for lakeside picnics. Summer weekends require a Central Cascades permit for popular routes.
Solo hikers savor quiet moments beneath alpine firs, while couples photograph mirrored lake reflections at dawn. Backpackers can link trails for multi‑day solitude, sleeping under brilliant constellations. Whether you want a challenge or a wander, the forest’s scale and variety accommodate every pace and preference.
Geology buffs and Instagrammers unite: this 54,000‑acre monument contains newborn obsidian flows, a 500‑foot cinder cone you can spiral‑drive to the top, and sister caldera lakes warmed by hot springs. Start at Lava Lands Visitor Center for ranger talks, then caravan south to Paulina Lake where beach picnic tables mesh with jaw‑dropping caldera walls. Groups can split between an easy shoreline loop, a waterfall hike, or renting pontoon boats big enough for a dance party. As daylight fades, the obsidian glass fields glow pearly silver – an otherworldly photo op.
Photographers love the soft golden-hour lighting through the trees, while runners and cyclists frequent the shaded trail for low-key workouts. Couples find cozy picnic nooks beside the river for midday escapes. You don’t need a big group to enjoy it, just bring a book, a hammock, or a curiosity for birdwatching.
When you need a break from Bend’s bustle, 20 minutes north lies Eagle Crest Resort and the high‑desert town of Redmond. Challenge your crew to a scramble at one of Eagle Crest’s three courses, junior tees keep it fun for beginners, then grab milkshakes at Redmond’s retro Taj Palace Drive‑In. The town’s Brewery District hosts open‑air concerts and food‑truck rallies on summer Fridays, while nearby Cline Falls offers cliff‑jumping for the bold (life jackets mandatory). Don’t miss Petersen Rock Garden’s quirky, hand‑built castles for group selfies that look lifted from a fantasy film.
Redmond charms couples with its art alley strolls and rooftop dining spots overlooking the mountains. Solo travelers can browse antique shops, then catch a midweek matinee at the restored Odem Theater. Nature lovers find early-morning solitude along the canyon rim trails. It’s a choose-your-own-adventure kind of day trip, no matter your vibe.
If your reunion crew leans luxury, swing out to Pronghorn, now rebranded as Juniper Preserve – for a spa and wellness day. Picture sunrise yoga on a lava‑rock platform, latte art classes at the clubhouse, and post‑massage mocktails by a zero‑edge pool overlooking the painted desert. Guided stargazing tours exploit Bend’s dark‑sky status; telescopes reveal Milky Way arcs impossible to see in cities.
Solo spa-goers can spend an entire day in peaceful silence, bookended by meditation walks and private sound baths. Couples gravitate toward couples’ massages and sunset cocktails by the firepit. Even a short visit offers deep restoration, perfect for travelers needing to recharge before the next high‑desert adventure.
| Day | Highlight | Morning | Afternoon | Evening |
| 1 | River & Downtown | Coffee at Sparrow Bakery; guided Big Eddy raft trip | Lunch & boutique stroll in Old Mill | Private chef taco bar at rental + hot‑tub soak |
| 2 | Mountains & Lakes | Drive Cascade Lakes Byway, hike Sparks Lake | Scenic chairlift brunch at Mt Bachelor; zip‑line or disc‑golf add‑ons | Bend Ale Trail by Bend Trolley (family friendly) |
| 3 | Volcano & Vines | Lava Lands Visitor Center + Paulina Falls | Paddleboarding on Paulina Lake | Sunset wine tasting at Faith, Hope & Charity Vineyards |
| Area / Property | Why You’ll Love It | Drive to Downtown |
| Widgi Elk Wonder | Peaceful, forest‑view home set right on Widgi Creek Golf Course; walk to Seventh Mountain Resort for dining & spa. Summer rafting, horseback riding, and hiking out the door; 5 min to Nordic trails and 15 min to Mt. Bachelor lifts. | ≈ 12 min to downtown Bend |
| Bend Hideaway – Unit A | Pet‑friendly retreat with private hot tub, arcade/media room, fenced yard & bikes; near Bend Country Club and “just minutes from the Old Mill District.” | ≈ 8 min to downtown Bend |
| Deschutes Landing at the Old Mill Riverfront | Steps to shops, dining, and river paths; river‑view balcony, gourmet kitchen, office nook, and Xbox/50″ smart‑TV media hub. Walk or bike the river trail to the heart of downtown. | 2–4 min drive / ~12 min walk to downtown Bend |
| The Osprey | Mountain views, large fenced yard with private hot tub, two dining areas, and trail access “to downtown” across from Tetherow Golf Club; minutes to Widgi Creek, Deschutes River & Mt. Bachelor shuttle. | 7–10 min to downtown Bend |
All Meredith Lodging’s homes include fast Wi‑Fi, professional housekeeping, locally roasted coffee starter kits, and access to 24‑hour guest support. Many are also pet‑friendly, have smart‑lock entry, and offer optional grocery‑stock or baby‑gear rentals.
At Meredith Lodging, we believe where you stay should feel as effortless and memorable as the time you spend there. That’s why our Central Oregon team carefully curates each home for design, comfort, and the flexibility to fit every kind of trip, from intimate escapes to large group gatherings.
Looking for a pet-friendly modern cabin, a downtown hideaway, or a spacious estate? We’ve got you covered, and we go beyond the booking with thoughtful extras like pre-arrival provisioning, concierge-style support, and mid-stay cleanings. Plus, every reservation supports our Meredith Gives program, helping fund local youth programs, veteran services, animal welfare, and disaster relief across the communities we call home.
Choose your dates, share your wishlist, and let Meredith Lodging handle the rest. A better stay starts here.
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