Make the most of the final days of summer with a relaxed 3-day Bend and Sunriver itinerary. Explore downtown Bend, Cascade Lakes, scenic trails, Sunriver…
September is one of the best times to explore Oregon, with sunny late-summer days in Central Oregon and crisp ocean air along the coast. It is the season for mountain views, farmers markets, live music, beach walks, local festivals, and slower days spent enjoying the places that make an Oregon getaway feel special.
Plan your Oregon getaway in Bend, Sunriver, Sisters, or Redmond, or head to the sandy shores of Lincoln City, Newport, Pacific City, Cannon Beach, and Manzanita. Meredith Lodging offers comfortable vacation rentals close to the experiences you came to enjoy, with stays across Central Oregon and along the Oregon Coast.
From comedy and concerts in Bend to kite-filled skies in Lincoln City, September brings plenty of reasons to plan a fall escape. Spend the day exploring, then come back to a private vacation home where you can relax, reconnect, and enjoy Oregon at your own pace.

Kick off Labor Day Weekend with three days of stand-up, improv, sketch comedy, and late-night shows during the Bend Comedy Festival. This nonprofit celebration of comedy and community is a fun choice for couples, friends, and anyone looking for an easy night out in downtown Bend.

Explore Bend’s creative side during the monthly First Friday Art Walk. Stroll through downtown galleries, meet local artists, browse special exhibits, and enjoy the relaxed energy of a fall evening. Pair it with dinner, drinks, or a walk along the nearby Deschutes River for a simple and memorable Bend outing.

Head to nearby Redmond for the Cascades Futurity & Aged Event, an equestrian competition hosted at the Deschutes County Fair & Expo Center. It is a great event for horse lovers, families, and travelers looking to experience another side of Central Oregon’s ranching and western culture.

September is still concert season in Bend. Hayden Homes Amphitheater has a full lineup planned, including Zach Top on September 10, Foster the People on September 12, and Riley Green on September 18. Make a night of it with dinner in the Old Mill District before enjoying live music beneath the Central Oregon sky.

Take a scenic drive to Sisters for the weekly farmers market at Fir Street Park. Browse micro-local produce, artisan goods, pantry favorites, and handmade finds while enjoying live music on select Sundays. It is a relaxed way to experience Sisters’ friendly small-town character.

Visit Sunriver’s final Saturday Market of the season for local produce, baked goods, art, and community shopping. The market runs from 9 a.m. to 1 p.m. and makes a wonderful addition to a September stay filled with bike rides, golf, forest walks, and time outdoors.

Make your beach walk a treasure hunt in Lincoln City. The city’s Finders Keepers program hides hand-blown glass floats along seven miles of shoreline throughout the year, giving beachgoers the chance to discover a one-of-a-kind Oregon Coast souvenir. Floats are placed during daylight hours, rain or shine, above the high-tide line and below the beach embankment.

Watch the skies over Lincoln City fill with colorful kites during the Fall Kite Festival. Held on the beach at D River State Recreation Site, this family-friendly event is a classic Oregon Coast experience, with dramatic ocean views, open sand, and plenty of room to settle in for a full day by the water. A special Finders Keepers float drop is also planned for the festival weekend.

Celebrate surf culture in Pacific City during the Cape Kiwanda Longboard Classic. This beachside event brings surfers and spectators together near one of the Coast’s most recognizable landmarks. It is a great reason to plan a Pacific City getaway, explore the shoreline, and enjoy the views around Cape Kiwanda.

For a day of music and coastal fun, head to nearby Waldport for the Beach, Bike & Blues Festival. It is an easy day trip for guests staying in the Lincoln City, Newport, or Depoe Bay area and offers a lively way to experience the local character of the Central Oregon Coast.

Enjoy a welcoming weekend of celebration and community during Newport Oregon Pride. Plan time to explore Newport’s bayfront, browse local shops and galleries, enjoy fresh seafood, or visit nearby coastal attractions before returning to your Meredith Lodging vacation rental.

Bring your four-legged family member to Muttzanita, a dog-friendly community festival and fundraiser in Manzanita. It is a fun option for pet-loving travelers staying farther north on the Coast, especially those planning a relaxing long weekend near Cannon Beach or Manzanita.
September is a beautiful time to choose your own Oregon adventure. In Central Oregon, spend your days hiking, biking, playing golf, exploring downtown Bend, or simply relaxing beneath the stars. Along the Coast, enjoy peaceful beach walks, local festivals, scenic drives, and cozy evenings with the sound of the Pacific nearby.
Meredith Lodging combines local expertise, professionally maintained vacation homes, direct-booking value, and 24/7 guest support, so you can spend less time planning the details and more time enjoying the destination.
For your Central Oregon escape, explore a Sunriver vacation rental near bike trails, golf, family attractions, and outdoor adventure, or find a spacious home for your Bend, Sisters, or Redmond getaway. Meredith’s Sunriver homes range from cozy cabins to larger vacation rentals near the area’s outdoor recreation. Choose an oceanfront Oregon beach rental, settle into a beachfront vacation home, or browse a stay with a hot tub, fireplace, or pet-friendly features. Meredith Lodging’s coastal collection includes homes in destinations such as Lincoln City, Newport, Cannon Beach, Manzanita, Seaside, Lincoln Beach, and Pacific City.
Plan a late-summer concert weekend in Bend, enjoy a peaceful Sunriver retreat, experience Lincoln City’s Kite Festival, or escape to the coast near Newport or Pacific City. Meredith Lodging has vacation rentals ready to help you make the most of September in Oregon.
Make the most of the final days of summer with a relaxed 3-day Bend and Sunriver itinerary. Explore downtown Bend, Cascade Lakes, scenic trails, Sunriver…
Plan a family summer getaway around the best lakes near Bend and Sunriver. Explore scenic spots for swimming, paddling, fishing, and picnicking, plus practical tips…
The Deschutes County Fair & Rodeo returns July 29-August 2, 2026 for its 105th year. Enjoy NPRA rodeo action, a FREE Sara Evans concert, carnival…
A sunny June day in Newport brings mild 65–70°F temperatures, bluebird skies, and nearly 16 hours of daylight. Start on the Historic Bayfront watching sea…
The Cannon Beach Sandcastle Contest (June 19–21, 2026; main contest June 20) transforms the iconic Haystack Rock shoreline into an open-air gallery of masterful sand…
Celebrate Labor Day with a getaway to the Oregon Coast or Central Oregon. Meredith Lodging offers vacation rentals in some of Oregon’s most popular destinations,…
Welcome to our last-minute vacation rentals page! Here you will find homes with availability this upcoming weekend and greatly reduced rates! This is your chance…