Leave Redmond around 7:00 AM via US-97 south, then OR-138 east through Diamond Lake Junction toward Crater Lake National Park. The drive takes about three hours, with limited services after Diamond Lake, so fill the tank and bring coffee, water, and snacks. Arrive through the South Entrance in late morning and park at Rim Village; September is quieter than midsummer, but parking near the lodge can still fill around lunchtime. Start with Rim Village and Sinnott Memorial Overlook, where paved, mostly accessible paths provide some of the best first views of the lake. Allow about 90 minutes, and bring a warm layer—the rim can be chilly and windy even on a sunny day.
Have lunch at the Crater Lake Lodge Dining Room, a particularly pleasant choice for its historic setting and lake views. Expect roughly $25–45 per person, and check the seasonal schedule before leaving since dining hours can change in September. After lunch, drive the West Rim route to Watchman Overlook. The short trail to the lookout is steep in places, so take your time; the viewpoint itself is worthwhile even if you decide not to walk all the way up. Allow 1–1½ hours, including the drive and time for photos.
Continue to Plaikni Falls Trail on the park’s south side for an easy-to-moderate two-mile round trip through quiet forest to a delicate waterfall. Wear sturdy shoes and carry water; afternoon shadows make this a comfortable hike after the exposed rim. Finish at Mazama Village Campground, where you can settle in and have dinner at the Mazama Village Café if open, or prepare picnic provisions purchased earlier in the day. Budget about $15–30 per person. Cell service is inconsistent, so download maps and confirm campground, road, and café status before departing Redmond; also keep an eye on NPS alerts for temporary closures or smoke conditions.
Leave Crater Lake National Park around 8:00 AM, allowing extra time for seasonal construction, wildlife, and viewpoint stops along Rim Drive before joining OR-62 toward Ashland. Keep the morning flexible—the road is wonderfully scenic, but September conditions and brief photo stops can easily stretch the roughly 2½–3-hour drive. Near Highway 138, stop at Toketee Falls for the short, moderately uneven forest trail to the famous two-tier waterfall; allow about an hour and wear shoes with good grip. There are no dependable meal services at the falls, so carry water and snacks from the previous day.
After continuing to Ashland, settle into the walkable downtown area and stretch your legs in Lithia Park. The creekside paths, landscaped gardens, and Japanese garden area are ideal for an unhurried 1½-hour stroll, with benches and plenty of shade. From the park, it is an easy walk up through downtown to Ashland Food Co-op for lunch or picnic supplies—allow about 45 minutes and budget roughly $15–25 per person. It is a useful stop for prepared foods, fruit, sandwiches, and drinks if you would rather eat outdoors than have a formal lunch.
Spend the late afternoon or evening at the Oregon Shakespeare Festival in downtown Ashland. Performances generally run about three hours, and schedules vary by production, so confirm curtain time and arrive 30 minutes early; downtown street parking can be limited, while public lots and hotel parking are usually more practical. If you have time before the show, browse the compact galleries and independent shops around East Main Street. Finish at The Peerless Restaurant, a short drive or roughly 15–20-minute walk from the festival area, for a polished dinner featuring regional ingredients. Reserve ahead, especially for a post-performance table; expect approximately $45–75 per person before drinks and tip.
Leave Ashland around 7:30 AM on US-199 toward Brookings, allowing roughly 3½ hours plus a fuel and restroom stop before the forest roads. Services become sparse near the California border, so top off in Grants Pass or Crescent City and keep water and snacks in the car. Your first stop is Jedediah Smith Redwoods State Park; park at the Stout Grove trailhead and take the easy, shaded 0.9-mile round-trip walk beneath enormous old-growth trees. Allow about 1½ hours, and wear shoes that can handle damp, uneven ground. A California State Parks day-use fee may apply, generally around $8–12.
From Stout Grove, continue slowly along Howland Hill Road, a narrow, mostly unpaved scenic road through some of the region’s finest redwoods. It is suitable for a regular passenger car when dry, but RVs and trailers should avoid it; expect pullouts rather than formal facilities and allow about an hour. Continue to Brookings for lunch or a short break, then spend the afternoon at Harris Beach State Park. The broad beach, offshore sea stacks, and rocky edges are excellent for an unhurried stroll—check tide tables before exploring tide pools, and stay well back from waves on the exposed rocks. Parking is usually straightforward, with a day-use fee often around $5.
Have an easy dinner at Zola’s Pizzeria in Brookings, a relaxed choice for pizza and salads at roughly $15–30 per person. Afterward, drive a few minutes to Chetco Point Park for sunset; the short paths lead to rocky viewpoints over the coast, and 45 minutes is enough unless the evening is especially clear. Bring a light jacket—the ocean breeze can make it feel cool even in September—and use a flashlight for the walk back if you stay through dusk.
Leave Brookings around 8:00 AM for the roughly three-hour drive south on US-101 to Bandon, treating the route as part of the day rather than rushing through it. Pull over only at signed viewpoints, since many roadside turnouts are narrow, and expect slow stretches through forest and coastal towns. Make Cape Blanco State Park your first substantial stop: the lighthouse area has expansive ocean views and easy walking, though the lighthouse itself may have limited seasonal hours. Allow about 1½ hours, bring a jacket, and check Oregon State Parks alerts before leaving—wind can be surprisingly strong even in September.
Continue a few minutes north to Port Orford Heads State Park, where the short coastal trails lead through low forest to dramatic headland views. The terrain is manageable but can be uneven, so sturdy shoes and trekking poles are useful; allow 1–1½ hours and keep well back from cliff edges. For lunch, drive into Port Orford and eat at The Crazy Norwegian’s Fish & Chips, a famously casual spot on US-101. Plan on roughly $15–30 per person, with counter-service timing that works well for a relaxed road-trip day; hours can vary seasonally, so verify before setting out.
After lunch, continue south on US-101 to Bandon, then head west toward Face Rock State Scenic Viewpoint. Give yourselves about 1½ hours to wander the broad beach and take in the sea stacks, arches, and changing light around Face Rock. Check the tide tables before walking far along the shore, and avoid climbing on wet rocks—this coast is beautiful but powerful, with sneaker waves a real hazard. If you arrive before check-in, leave luggage locked out of sight and use the signed parking areas rather than improvised beach pullouts.
Finish in Bandon’s Old Town at Tony’s Crab Shack, an easygoing waterfront choice for crab, fish, and other local seafood. Dinner is generally about $25–45 per person, and counter-service seating keeps the evening uncomplicated after a full day outside. Old Town is compact, so park once and stroll along the waterfront afterward if energy allows; sunset comes early enough in mid-September to catch the last light without making dinner late.
Start early from Bandon for Bandon Marsh National Wildlife Refuge, allowing about 20 minutes to reach the North Bandon access area. The refuge is best in the morning, when the mudflats and marsh channels are active with shorebirds; plan on roughly an hour of easy walking and birding. Bring binoculars, water, and a light jacket, and check the refuge’s current access information before leaving—facilities are limited and trails can be damp. Afterward, drive about 25 minutes north to Coos Bay for the Coos History Museum, which typically opens late morning; allow 1½ hours for its exhibits on the region’s logging, maritime, and Indigenous history. Admission is generally modest, around $5–10 per adult, but confirm hours because museum schedules can vary by season.
Walk or drive a few minutes through central Coos Bay to 7 Devils Brewing Co. for lunch. This is an easygoing local stop with burgers, sandwiches, salads, and house beers; budget approximately $20–35 per person. Keep lunch to about an hour so there is time for Shore Acres State Park, a 15-minute drive west in Charleston. The park’s formal gardens and cliff-top viewpoints make a fitting final coastal stop, with paved paths and short walks rather than a strenuous hike. Allow 1½ hours, and bring a windproof layer—the headlands can feel considerably cooler than town. Oregon State Parks day-use parking is usually about $5, payable at the entrance or by parking pass.
Leave Shore Acres State Park or nearby Coos Bay around 1:30 PM for the drive back to Redmond via US-101, OR-42, and US-97, allowing roughly 4½–5 hours plus a brief break. Roseburg is a practical place for coffee, fuel, or a restroom stop before the longer stretch east; after that, services become more spread out as you cross the Umpqua National Forest. Check TripCheck before departure for OR-42 and US-97 conditions, especially after rain or if there are active road projects. Expect an evening arrival in Redmond, so it is worth fueling before leaving Coos Bay and keeping water and snacks in the car.