First highway you drove on

[golden eagle]

I believe the first highway I drove was either US 49 or US 80. It's been so long ago, so I can't quite remember. I first drove on an interstate in high school. It was I-20.

[Quillz]

Probably the 101.

[Ian]

Now that I'm driving, I can contribute to this 

First highway I ever drove on was PA 352, first freeway was I-476.

[corco]

Ohio 41 when I was 11 in my Grandpa's pickup (8?/1999).

Legally- probably US-20/26 through Boise (5/2003).

First freeway was I-184 through Boise (5/2003).

First highway I drove by myself would be Idaho 55 (11/2003).

First highway I took pictures of while driving is Washington 163 (1/2007).

[Duke87]

Er, I assume we mean behind the wheel? Either CT 104 or CT 137. I don't remember the moment, didn't consider it noteworthy, but logically it would have to be one of those two.
First freeway would be the Merritt Parkway (CT 15), gotten on northbound from CT 104 northbound (exit 34) - that moment I remember, I almost hit the guardrail failing to merge properly!
First interstate... probably I-95 but possibly I-91, oddly - I remember a trip my father and I took to the New England Air Museum while I was still on my learner's permit which was the first trip of significance that I drove on, and I can't say with 100% certainty that I'd been behind the wheel on I-95 (which is considerably closer to where I live) before that.

[rawmustard]

Considering I took driver's training in Coldwater, it would have to be US-12, if my first road lesson didn't take me to I-69 via the Jonesville Road interchange, which I don't think happened.

[golden eagle]

Er, I assume we mean behind the wheel?

Yep

[hbelkins]

Had to be KY 52, since that's the road I lived on when I was 16.

First freeway would have been the Mountain Parkway, first US route US 25/421, first interstate I-64.

[agentsteel53]

probably I-95/MA-128 or US-1 within minutes of each other, with a potential I-93 in there as well.

[v35322]

First Interstate was I-25 in Colorado Springs.

First U.S. Highway (other than 85/87 since they overlap I-25) was probably U.S. 24.

First CO State Highway was probably 83, back when Academy Boulevard still had that designation.

[Hot Rod Hootenanny]

Either Oh 38 in Madison County or Oh 4 in Union County. I must of been 9 at the time.

[roadfro]

First Nevada route: Best guess would be SR 574 (Cheyenne Ave), as it's the closest route near my house in Las Vegas.

First US Highway (and freeway): US 95 in northwestern Las Vegas.

[xcellntbuy]

First main highway:  US 9 in Columbia County, New York
First limited access highway:  Taconic State Parkway following south to the Saw Mill River Parkway, the Henry Hudson Parkway and the remaining sections of the West Side Highway.

Quite a contrast and an experience I will never forget.

[Central Avenue]

First numbered highway would have been OH 16.

First US highway would be US 40.

First Interstate and also first freeway would have been I-270.

[Brandon]

Illinois 53 and I-55.

[mobilene]

The St. Joseph Valley Parkway (as it is now called - back in 1984 when I first drove it, it was just "the bypass") around South Bend, IN.

[Michael in Philly]

I assume 600-series New Jersey county roads don't count, particularly as the county I grew up in wasn't bothering to mark those in those days.  So, most likely US 22, which I lived a block from.  But possibly NJ 28.  First freeway or expressway, no idea.

[1995hoo]

The Beltway within a week of getting my learner's permit when I was 15, once my dad had decided that I could downshift well enough to be allowed on the Interstate.

But if by "highway" you mean any numbered road other than the trivial (recognizing that in Virginia almost every road bears a number), then VA-236, which is the most direct route from my old high school (where my dad started teaching me to drive in the big car park) to my parents' house. 

[Dr Frankenstein]

On learner's permit: That would be QC-236 (all of it) and then QC-132 between Saint-Anicet and Saint-Stanislas-de-Kostka.
Freeway on learner's permit: A-15.
On full license (with teen restrictions, which I have until age 25), alone: Apart from the bits of QC-132 and 236 in my commute to college, that would have be QC-132 to A-30 (Châteauguay section) to QC-132 (through St-Constant and Delson) to A-30 to A-10 to A-55 to QC-108.
First driven as a roadgeek with a camera: QC-138 through Ste-Martine and Mercier, and the new section of A-30 in St-Constant.

[Super Mateo]

US 45 and I 80; back when that intersection was a cloverleaf.

[Bryant5493]

Probably Georgia State Route 279/Old National Highway.


Be well,

Bryant

[nexus73]

US 101.  At the age of 14 with no license or even learner's permit, my friend of the same age as me and I drove this old man who had a new 1970 International 3/4 ton pickup with a 4-speed from Gold Beach OR to Crescent City CA on a Sunday drive to get the old man a bottle of booze, which was not available in Oregon since it was Sunday and the OLCC liquor stores were closed.  That was also my first time out of the state of Oregon!  I had never even driven a manual transmission vehicle before but I took to driving like a duck to water.

What wasn't expected and scared me: The original Chetco River bridge was a very narrow late 1920's style affair.  Coming from the other direction was a log truck.  I figured since vehicles had been going across the bridge in both directions for decades, that I would be able to do it.  I did but I drove at 10 MPH...LOL!  The other scary thing to encounter was the construction of the freeway 101 section north of Crescent City.  That was a Real Big Deal, massive (to a 14 year old making his first drive) in scope with tons of equipment and dust, trying to figure out my way through the construction zone.  I did so without mishap.

I made the drive down and my friend asked if he could drive as we headed back.  I let him do so.  He lasted all of six miles and was happy to hand the wheel back to me.  That was my introduction to driving and I never looked back!

Rick

[sandwalk]

For me, it would probably be Ohio SR-4 in Erie County (the hospital I was born at was located there LOL). 

For my first personal driving experience, it would be Ohio SR-113 in Erie County.

[allniter89]

I took drivers ed back in '69 (yes they had cars back then  ) in Fayetteville, NC so my first highway was likely US 301. That was b4 I 95 was finished in the area and all traffic followed US 301 thru town. 95 was likely my first driven interstate tho I dont have a definite recollection of it.
What was your first roadtrip over 300 miles you drove, from where to where?
Mine was Fayetteville, NC to Detroit, MI in 1969, dad allowed me to pick the route and drive the entire length. I cant recall the exact route but I remember Winston-Salem, US 421 thru sw VA and adjacent KY to Richmond, KY then I 75, M 39, and Plymouth Rd to 9529 Piedmont phone BR30269. good times, good times!

[ftballfan]

First numbered highway and first freeway driven would have to be US-31 for me.
When I was 15 I drove my father's truck which was pulling a U-Haul from Manistee to Holland to take my sister to college. Needless to say, that was very interesting.