Hiking out of Cape Lookout State Park the trail is well maintained and well marked.
The trail takes you up and over the Cape, without taking you out to the end, before dropping you back off on the beach.
Follow the beach south until the mouth of Sand Lake, which should be forded at low tide. During the summer months this is a bit easier. At high tide it is impassable. If this is the case you'll have to hike out the alternate route, which is a road walk out Galloway Rd back to Three Capes Highway.
At some point you will be able to return to the beach just north of Cape Kiwanda State Natural Area.
After climbing up and over Cape Kiwanda the trail follows the beach south, though you will see stores and restaurants on your left tempting you away from the beach. Follow the beach until you see a beach access road that will bring you back towards the main road, crossing a short bridge for the long road walk back out to 101 and south to Winema Beach.
An option here is to take the bus.
From Pacific City there is a bus that will take you directly to Winema Beach, or further into Neskowin, or even further into Lincoln City.
After the road walk you return to the beach at Winema Beach, which is best hiked at low tide, until you get to Neskowin Beach State Recreation Site. Here you will have to return to 101 for short road walk to the Falls Creek Trailhead, which will take you over Cascade Head.
Following the OCT at this point will not give you the best views from Cascade Head however, so you may consider hiking off trail a bit to see some spectacular views.
Once you are back on the 101 follow that south into Lincoln City, returning to the beach at NW 39th St. just south of the Safeway. Follow the beach south until you get to the Siletz River where you'll have to hike back in to the 101.
If you plan on staying at the hiker/biker camp at Devil's Lake State Recreation Area, you'll have to get off the beach before that. The best landmark for finding the campground from the beach is to hike south until you hit D River about halfway through Lincoln City. Looking to your left you will see 101 crossing a short bridge over the river. Return to 101 here and Devil's Lake SRA is just a short distance north.
Right near where the OCT returns to 101 at Siletz Bay on the southern end of Lincoln City is a bus stop at Taft IGA. From here you can catch either the Lincoln City Loop bus or the bus heading south towards Newport. If you'd like to skip the long road walk south of Lincoln City heading through Depoe Bay, a great place to get off is the Devil's Punch Bowl State Natural Area. Just tell your bus driver first so they'll know to stop. From there you can hike down to the beach and either enjoy a good days hike to South Beach State Park, or take it easy and stay at Beverly Beach State Park.
Otherwise it's a road walk right off Map #3 into Map #4.
Where to Stay
Cape Lookout State Park has one of the best hiker/biker camps in the state. (In my opinion.)
From Cape Lookout State Park to Devil's Lake State Recreation Area it is 51 miles along Sand Lake Rd. and 101. For a thru hiker that means that you will most likely have to stealth camp somewhere in between for at least one night, maybe two if you can't manage two 25 mile days.
For a short hike after Cape Lookout:
Sandbeach Campground by Sand Lake, which is mostly for dune buggies might be an option, but I have never personally stayed, nor known anyone who has.
There are also campgrounds on the other side of the alternate route around Sand Lake, Near Pacific City:
Webb County Campground - has tent sites and a hiker/biker option - call to be sure
33005 Cape Kiwanda Dr, Cloverdale, OR 97112
Cape Kiwanda RV Resort - has ten tent sites, but is more expensive
33305 Cape Kiwanda Dr
Pacific City, OR 97135
Further inland: Woods County Campground/Park., (503) 965-5001 - which says that it has a hiker-biker option on the Tillamook county website, but could find no information on tent sites. Their address is 34060 Brooten Road, Cloverdale, OR 97112
Further south in Neskowin camping might be an option at the Neskowin Creek RV Resort, but again, I have never stayed there, so call to find out if they still take hikers. Their address is 50500 South Highway 101, Neskowin, OR, 97149, (503) 392-3355
Hopefully you did a major Resupply in Tillamook so that you still have food left when entering Pacific City.
Coming off Cape Kiwanda and back down to the beach there is a small market place for the Cape Kiwanda RV Park which offers some light resupply.
Stock up here with enough food to make it the rest of the way to Lincoln City. This will vary depending on whether you plan on doing the road walk or taking the bus.
There is also Ben and Jeff's Burgers and Tacos and Doryland Pizza in this same block.
Further south on the OCT you'll have to head inland back to 101. This brings you past a Shell Gas Station and a Mexican food restaurant, and these are your last options until Lincoln City with the possible exception of the Cafe at Hawk Creek in Neskowin.
Luckily in Lincoln City it is possible to do a major resupply. Right on 101, and the OCT before you turn on 39th St., is not only a Safeway, but a Grocery Outlet, a Rite Aid, a Walgreen's, a McDonald's and a Pig 'N Pancake.
There are more options throughout the city and closer to Devil's Lake State Recreation Area. Just before leaving Lincoln City there is also Kenny's Food Market just before SW 50th St. near where the the OCT leaves the beach and returns to 101.
But you wont need much food to make it to Newport. A two day supply early in the day will get you through your first day in Lincoln City and the next into Map #4.