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US 199 was among the inaugural 1926 routes, and it has connected the same cities ever since.  US 199 is one of only four US routes whose implied "parent" route (in this case US 99) has been completely decommissioned:

Originally US 199 ended at the intersection at lower left, known as "Redwood Junction".  Following is an historic photo taken at that junction; this sign was probably posted on 6th Street, for the benefit of traffic on northbound US 99.  North is to the right, so the photo was taken looking west.  Just to the left is where 6th forks to either Rogue River Highway or Williams Highway, so US 199 traffic heading that direction would have quickly taken a right turn in order to follow Redwood Highway:

After I-5 was built through Grants Pass in about 1965, the US 199 designation was extended north with hwy. 99, and then east to its terminus at interchange 55:

​(At some point, US 99 was decommissioned and replaced with OR 99; and also 7th Street became a one-way partner with 6th Street to carry hwy. 99 traffic.)  These photos were taken from southbound I-5 at the north beginning of US 199:

Drivers exiting there are given directional signage at the bottom of the offramp:

The assembly pointing right should say "US 199; To OR 99".  Travelers turning right at that point will soon see the first southbound US 199 marker...

...but if one were to go left at the bottom of the off-ramp, they would be at the north end of US 199, where the only options are to go north or south on I-5:

Modern US 199 follows a relatively recent extension eastward from Redwood Junction, via a third bridge over the river, called Grants Pass Parkway.  ​Traffic joins "old" US 199 (E Street) about a half-mile west of I-5, so the north terminus of US 199 did not change after the Parkway was built:

The northernmost marker was in error, showing "OR 199" instead of US 199:

By the mid-1940s, US 101 had been rerouted to its current alignment southward as far as today's junction with US 199.  From that point, it continued south on what is now English Lane, and then followed Parkway southwest into town.  So then US 199 ended on Parkway at English.  Here, we are looking south on Parkway:

Originally that was all US 199, and it ended at US 101 in town, about three miles ahead.  But later US 101 was rerouted such that it came in from the right on English, and then continued ahead.  So US 199 was truncated to end at that intersection.  Today, to the right on English is not a through road -- it was vacated when the US 101 freeway was built:

It is unclear why only one of those panels was replaced, and it is unfortunate that old button copy is no longer with us. 

Anyway, from that exit there are no ramps that directly connect to northbound US 101; a right turn ahead puts travelers on a connector road.  That same connector is used by southbound 101 traffic wanting northbound US 199 (which is why the sign says "TO US 199"):

It is not so complicated heading north on US 101, but here too more button copy has now bitten the dust:

​The confirming marker on the offramp is shown close-up below...

​This photo shows the first confirming marker on mainline US 199.  The highway immediately enters the redwood forest visible in the background, and makes for a scenic drive through canyons and over passes all the way into Oregon: