First type of route you have driven

[Pete from Boston]

First road ever: some random dirt roads in Phippsburg, Maine.

Phippsburg!  Not a place I hear a lot about.  I was a regular camper at Hermit Island until my particular group of campers disintegrated.  I miss it there.

[allniter89]

 Altho it was 46 yrs ago I'm sure these are accurate 
Interstate: 75 Richmond, KY. We jumped on 75 from US 421(?) on my 1st long distance drive, Fayetteville, NC to Detroit, MI to Ft Lauderdale, FL in 1969. Dad let me plan the route, I dont remember the exact routing but we went from Fayetteville thru Winston-Salem north into VA thru Big Stone Gap, VA to Richmond, KY.

US Route: 301, Fayetteville, NC
State Route: NC 87. My bedroom window faced the intersection of NC87& Honeycutt Rd, Ft Bragg, NC. I saw alot of serious crashes there.
County Route: Kent 368, DE.
Canadian Hwy: ALB 2(?) from the MT line enroute to Alaska 1965. I didnt drive this one I was only 12 yrs old but I wish I could have.
I had my own Kodak Instamatic camera & I took alot of pictures enroute to Alaska but they were lost in the tornado, Little Heaven, DE. June 77

[Jardine]

Interstate:  29 (2di) and 480 (3di)

US 75  (since relocated out of state, btw)

Iowa 183

County would have been an unmarked at the time dirt road. 

[JCinSummerfield]

Here are my probables.  I started driving in 1980.

Interstate - I-94
US Route - one of these four: US-12, US-23, US-27 or US-127.  Of course, US-27 in Michigan is now US-127.
State Route - M-52
County - D-19?

[jemacedo9]

Interstate:  I believe it was I-95 in far eastern CT eastbound
US Highways:  US 202 in PA
State Highways:  I lived on PA 113
Signed County Route:  this I don't remember, but if I had to guess, NJ Co Rt 541

[CtrlAltDel]

As I grew up in a major metropolitan area, these routes don't come from my direct recollection, but from inference.

2di : I-88
3di : I-290

US : US-12/US-20/US-45

IL : IL-56

[doorknob60]

Interstate: I think I-84, may have been I-5 though.
Bonus 3DI: I-205 (Portland)
US: US-97 most likely; possibly US-20. Both within Bend city limits.
Bonus 3DUS: US-197.
State Route: Tough one. Probably OR-126 if you count its overlap with US-20 from Sisters to Santiam Pass. If not, maybe OR-22. Could also be OR-35 maybe.
County: No idea, those aren't really signed around here.

[Thing 342]

Interstate: I-64
US Highway: US-17
State Highway: VA-143
County Highway: No idea, maybe Morgan, WV CR-7.
Secondary Highway: York, VA SR-1800.

[bing101]

Here are my first roads that I driven

I-80
CA-37
US-50


Business 80 Sacramento.

[Buck87]

Interstate: 80 & 90 together (Ohio Turnpike)
US route: 20
State route: It's definitely one of these four, but I have no idea which one: OH 18, OH 113, OH 269, OH 4
County Road: Bismark Rd (Huron County - which has named roads with mostly hidden numbers)

[sbeaver44]

Interstate: almost certainly I-81
US Route: US 15
State Route: probably PA 641
County Route: we don't really have these in PA, so I have to think... Possibly CR 857, Morgantown, WV

[DTComposer]

All of these were within a week of getting my license:

2di Interstate: I-80
3di Interstate: I-880
US Route: US-101
State Route (freeway): CA-17 (within an hour of getting my license)
State Route (non-freeway): CA-9
County Route: G-10

[Ian]

First road ever: some random dirt roads in Phippsburg, Maine.

Phippsburg!  Not a place I hear a lot about.  I was a regular camper at Hermit Island until my particular group of campers disintegrated.  I miss it there.

That's funny! Me and my family always like to go to Sebasco every summer around Independence Day, so I drove on a few back roads there a few weeks before my 16th birthday. Beautiful area!

[Vizier]

Interstate: I-105 (Eugene, OR)
US Highway: US 20 (Albany OR)
OR State Route: OR 99/126 (Eugene OR)

[MisterSG1]

Even though I'm from Canada, I'll conform to the restriction and take a trip down memory lane:

First 3di - I-190 in Niagara Falls, NY
First 2di - I-94/I-69 in Port Huron, MI
First US route - US-62 in Niagara Falls, NY

First Provincial/State Route (non-freeway) - *tough one* Ontario Highway 89 in Alliston, ON
First Provincial/State Route (freeway) - Ontario Highway 410 in Brampton, ON
First County/Regional Route - Airport Road in Brampton, ON (Peel Regional Route 7)

[silverback1065]

first driving lesson I-465

[roadman65]

Garden State Parkway as Clark, NJ had no numbered routes as first freeway in Drivers Ed.
It would have to be either US 1 or US 22 for US routes.
Definitely I-78 for interstate.  I drove that one with my permit before I got my license.

[Max Rockatansky]

Well over two decades ago:

US 202:  Downtown New Milford, CT
I-84:  Downtown Danbury, CT
CT 133:  Downtown Bridgewater, CT
No idea on the county route, I don't recall any being signed in the area.

[leroys73]

I-44 or I-70.  Probably I-44 as it was replacing US 66 in MO. That was a long time ago and difficult to remember.

US 62

Oklahoma 7

Some unmarked county road that was probably dirt.

[Takumi]

Interstate: I-95
US: US 1/301 concurrency
State: VA 144
Secondary (since Virginia doesn't have county routes): probably Chesterfield SR 620

[Super Mateo]

Interstate: 80
US Route: 45 (or 6 if permit driving doesn't count)
State: IL 7 (IL 43 if permit driving doesn't count)
County: ??? Cook County never signed them until recently, and even now there isn't a whole lot of noticeable signage.

[signalman]

Interstate: 80
US Highway: 46
State Highway: Either NJ 10 or 15, don't remember which was first
County: Either Morris Co. 661 or 664, both are close to where I grew up and both are plausible.  I'm not sure which I drove first.
Local/Municipal: The street that I grew up on

[RobbieL2415]

Interstate: CT, I-291
US Route: US 6, Mid-Cape Highway
Limited-access SR: CT-2
Surface SR: CT 30
County Route: n/a, none exist in CT and I've yet to do a road trip that necessitates me taking one.
Toll Road: Mass Tpke

[Henry]

US 41, I-90/I-94 and IL 50

[Halian]

As best I can remember...

2di: 40, unless you count business interstates, in which case Bus40/NC
3di: 175/FL, I think
2dus: Either 52 or 92
3dus: 158
SR: NC 66
CR: 4146 (Volusia County, FL)