Bend, Oregon is a dream for families, foodies, and adventure-lovers with amazing mountain views and tons of sun! We spent one amazing week here in an Airbnb to reset, recharge, and restock—and we loved how walkable and bikeable the city is! There are a lot of options to explore in Bend so don’t miss this stop on your roadtrip.
Whether you’re traveling with toddlers or looking for an outdoorsy reset, this itinerary is packed with ideas for your next visit to Central Oregon. Plus, Bend is incredibly bike-friendly, with miles of paths and wide streets—perfect for hauling the kids in a bike trailer or cruising solo.
Where We Stayed
We booked an Airbnb just a short walk (or ride!) from downtown Bend. Thanks to Bend’s amazing bike infrastructure, we were able to bike to nearly everything—breweries, food trucks, parks, even gelato runs.
Breweries & Food Trucks
Bend is famous for its brewery culture—and we were thrilled to find so many that welcomed our toddlers and dogs, offered space to roam, and were easily accessible by bike:
- Bend Brewing Company – lovely riverside spot
- The Lot – a laid-back food truck pod
- 10 Barrel Brewing Co. – nice outdoor space with firepit
- Podski – another great food truck hub
- Crux Fermentation Project – large lawn with food trucks and great beer selection
Yes, we biked to every single one of these from our Airbnb!
Coffee & Work Spots
Whether it was catching up on emails or fueling up for the day, these coffee shops were clutch:
Parks & Playgrounds:
- Harmon Park – toddler-friendly and super close to downtown
- Pilot Butte State Scenic Viewpoint – a playground at the base of the hike
- Columbia Park – cute playground with a ship structure and long slide
- Farewell Bend Park – riverside playground and trail system
- Park next to Active Culture – great dinner spot + play area
Museums & Learning:
- Play Society – indoor play space for little ones
- High Desert Museum – wildlife, hands-on exhibits, and nature learning for all ages
Hikes & Outdoor Explorations
- Pilot Butte – 0.5 miles up for a city view of Bend
- Shevlin Park – our 2-mile loop was perfect for toddler biking and hiking
- Wychus Overlook Trailhead – a scenic and secluded 1-mile loop outside of Sisters
Final Thoughts
Bend gave us everything we needed—great food, outdoor adventures, space for ourselves and our kids and dogs, and time with friends. If you’re looking for a balanced week where both parents and kids get their fill, Bend is your spot.
Have questions about any of these places? Drop a comment or message us on Instagram at @TruckCamperFamily or contact us via email at truckcamperfamily@gmail.com.
If you have time, check out neighboring towns – Sisters, Redmond, and Sunriver!
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