Streets named for a town they point in the direction of

[SkyPesos]

I wonder if the OP had a slightly different idea in mind for this thread. His example merely points towards Milwaukee, and it doesn't come anywhere close to reaching it. Most (if not all) of the other examples don't really fit that description. Perhaps this thread would be more interesting if we only regarded examples that don't reach the place they are named after.

An example of this would be Beaumont Highway on the east side of Houston. It points towards Beaumont, but doesn't reach it.

In that case, Cleveland Ave in Columbus could qualify. Though part of it is also part of OH 3, which does reach Cleveland (not under the "Cleveland Ave" name though).

[SEWIGuy]

I wonder if the OP had a slightly different idea in mind for this thread. His example merely points towards Milwaukee, and it doesn't come anywhere close to reaching it. Most (if not all) of the other examples don't really fit that description. Perhaps this thread would be more interesting if we only regarded examples that don't reach the place they are named after.

An example of this would be Beaumont Highway on the east side of Houston. It points towards Beaumont, but doesn't reach it.

What IS interesting about the OP's example, is that while Milwaukee Street does point toward Milwaukee, I don't think it was ever the way that traffic would actually take to get to Milwaukee from Madison.

It ends at a T-intersection just outside of the city, at pretty much the same spot it has always ended.  It has never carried a US or state route designation either.

[ran4sh]

I wonder if the OP had a slightly different idea in mind for this thread. His example merely points towards Milwaukee, and it doesn't come anywhere close to reaching it. Most (if not all) of the other examples don't really fit that description. Perhaps this thread would be more interesting if we only regarded examples that don't reach the place they are named after.

An example of this would be Beaumont Highway on the east side of Houston. It points towards Beaumont, but doesn't reach it.

My first thought was Fayetteville Rd in Rockingham NC, which is US 1 north from that city, and I always thought that people use US 74 to US 401 to reach Fayetteville from Rockingham, but it turns out that Google Maps actually suggests a route that starts off using US 1.

[Dirt Roads]

Close into Charlotte, North Carolina, we don't see this so much.  More prevalent around the outskirts.  Going around the city twice to get all of the candidates.

Charlotte, near uptown(clockwise, twice around)
Statesville Avenue
Providence Road

Charlotte, way out of town(clockwise, twice around)
Statesville Road
Old Statesville Road
North Tryon Street becomes Concord Road
Albemarle Road
Seventh Street becomes Monroe Road/Old Monroe Road
Third Street becomes Providence Road
South Boulevard becomes Polk Street (in Pineville) then becomes Lancaster Highway
South Tryon Street becomes York Road (which zig-zags up into Lake Wylie before turning back south)
West Street becomes Steele Creek Road

[DTComposer]

The three that come to mind in Santa Clara County:

-Oakland Road, leaving San Jose pointing towards Oakland (this was CA-17; street renames upon entering Milpitas and beyond, and is no longer continuous with other portions of the historic route)

-Monterey Road/Highway, leaving San Jose pointing towards Monterey (this was US-101; although you have to leave US-101 to eventually get to Monterey)

-Saratoga Avenue, leaving Santa Clara pointing towards Saratoga (see below)

-Santa Cruz Avenue in Los Gatos qualified at one time as it continued onto Santa Cruz Highway, but the name now ends as it it merges with the CA-17 freeway/expressway.

Not super common out here but the City - City Road examples do exist. Kiowa-Bennett Road jumps to mind.

Chris

Santa Clara County used to have a lot of the City-City names, most of which have been re-named:

Saratoga-Santa Clara Road -> Saratoga Avenue
Santa Clara-Los Gatos Road -> Winchester Boulevard
San Jose-Los Gatos Road -> Bascom Avenue*
Los Gatos-Almaden Road -> same
Saratoga-Los Gatos Road -> same (cities reversed on portion)
Saratoga-Sunnyvale Road -> same (cities reversed on portion, portion re-named De Anza Boulevard)
Mountain View-Alviso Road -> CA-237 (freeway) (this name still exists on a BGS on US-101)
Alviso-Milpitas Road -> CA-237 (freeway)
Santa Clara-Alviso Road -> Lafayette Street

*the continuation of this street into Los Gatos, now called Los Gatos Boulevard, was previously called San Jose Avenue, which would have qualified. It was renamed around 1970.

[Evan_Th]

Pretty common in this part of North Carolina:

Raleigh (clockwise): 
Wake Forest Road
New Bern Avenue
Garner Road
Wilmington Street
Fayetteville Street (doesn't go out of the city anymore)
Chapel Hill Road
Hillsborough Street
Creedmoor Road

Durham (clockwise):
Roxboro Street/Roxboro Road
New Raleigh Highway
* didn't include Miami Boulevard
Fayetteville Street/Fayetteville Road
Old Chapel Hill Road
Chapel Hill Street/Chapel Hill Road
Hillsborough Road

Similarly in Chapel Hill/Carrboro:

Old Durham Rd
Farrington Rd
Raleigh Rd
Pittsboro St (ends at Columbia St which continues toward Pittsboro)
* didn't include Greensboro St
Old Greensboro Rd
Old Fayetteville Rd (dead-ends at University Lake
Hillsborough Rd
Hillsborough St (ends at MLK Blvd which continues toward Hillsboro)

[Dirt Roads]

Durham (clockwise):
Roxboro Street/Roxboro Road
New Raleigh Highway
* didn't include Miami Boulevard
Fayetteville Street/Fayetteville Road
Farrington Road
Old Chapel Hill Road
Chapel Hill Street/Chapel Hill Road
Hillsborough Road

Similarly in Chapel Hill/Carrboro:

Old Durham Rd
Farrington Rd
Raleigh Rd
Pittsboro St (ends at Columbia St which continues toward Pittsboro)
* didn't include Greensboro St
Old Greensboro Rd
Old Fayetteville Rd (dead-ends at University Lake)
Hillsborough Rd
Hillsborough St (ends at MLK Blvd which continues toward Hillsboro)

Great list.  You picked up one that I forgot, except that Farrington Road should be included in the Durham list (as it branches off from Old Chapel Hill Road, then sneaks through the northeast corner of Chapel Hill that happens to be in Durham County).  On the other hand, if you treat Chapel Hill like a metropolis then you ought to be able to include the other Farrington Road, which branches off US-15/US-501.  That road starts out as Mount Carmel Church Road in Orange County, then changes names to Farrington Road at the Chatham County line.  Unlike the Durham version, this one actually takes you down to Farrington and further to Farrington Point.

[US20IL64]

Chicagoland

IL-21, aka Milwaukee Av, from central Chicago to Gurnee IL, part of old trail to MKE.

IL-131 Green Bay Rd, used to connect to Clark St in Chicago, another old trail to WI.

IL-19, used to be called 'Chicago-Elgin Rd', now starts as Chicago St. in Elgin and Irving Park Rd, through burbs into city.

IL-58, Golf Rd, used to be known as 'Evanston-Elgin Rd'.

Old US-66, Joliet Rd before bypasses.

[plain]

The few in Richmond for the most part goes to CDPs in the suburbs, and continues through them rather than just to them, so I don't think they're very good examples.

A surefire one is Williamsburg Rd, which is US 60 heading east towards Williamsburg.

Likewise, Williamsburg has Richmond Rd, which is US 60 heading west towards Richmond.

[JCinSummerfield]

I'm not sure what we're looking for, but I'll throw this out:  In Monroe County, Michigan there is Ida-Maybee Rd.  Running south, it ends before it reaches Ida, MI.  Running north, it goes west of Maybee, MI.  Doesn't reach either municipality.

[Bruce]

Only a handful of urban cases here that I can immediately think of:

Seattle: Bothell Way (SR 522)

Kirkland: Redmond Way

Tacoma: Puyallup Avenue (sort of)

Portland: Vancouver Avenue

Plenty of rural ones, especially with X-Y Road names.

[epzik8]

In Baltimore:

Reisterstown Road (MD 140) goes northwest toward Reisterstown.
York Road (MD 45) goes due north toward York, Pennsylvania.
Belair Road (US 1) goes northeast toward Bel Air.

Bonus: Harford Road (MD 147) goes northeast into Harford County.

[Dirt Roads]

Plenty of rural ones, especially with X-Y Road names.

I wasn't including any of North Carolina's X-Y roads.  Case in point, the main road between Durham and Chapel Hill (US-15/501) is Durham-Chapel Hill Boulevard.  Needless to say, that's the highway that replaced Old Chapel Hill Road/Old Durham Road.  I've only encountered a few of these X-Y roads leaving the larger cities in North Carolina.

[GaryA]

In Baltimore:

Reisterstown Road (MD 140) goes northwest toward Reisterstown.
York Road (MD 45) goes due north toward York, Pennsylvania.
Belair Road (US 1) goes northeast toward Bel Air.

Bonus: Harford Road (MD 147) goes northeast into Harford County.

I followed MD 140 for an outing one time, and it was an interesting assortment of roads named for towns, most of which were the next relatively large town outbound from Baltimore (skipping over a couple of "Main St" names):

Reisterstown Rd
Westminster Pike
Baltimore Blvd
Taneytown Pike
Baltimore St
Taneytown Pike
Waynesboro Pike

[Flint1979]

All over the place here.

[TheStranger]

I wonder if the OP had a slightly different idea in mind for this thread. His example merely points towards Milwaukee, and it doesn't come anywhere close to reaching it. Most (if not all) of the other examples don't really fit that description. Perhaps this thread would be more interesting if we only regarded examples that don't reach the place they are named after.

An example of this would be Beaumont Highway on the east side of Houston. It points towards Beaumont, but doesn't reach it.

Some California examples:

Oakland Road (former US 101E, Route 17, later Route 238) in San Jose

San Jose Avenue (including a portion of former US 101/current Route 82) in San Francisco, which was the historic "San Jose Road"

Old San Francisco Road in Sunnyvale

San Mateo Avenue in South San Francisco/San Bruno

Stockton Boulevard in Sacramento & Elk Grove

Auburn Boulevard in northeast Sacramento/Citrus Heights/Roseville

Marysville Boulevard in Sacramento's Del Paso Heights and Robla areas

Concord Avenue in Brentwood

[DenverBrian]

Don't forget all the freeways in California! Santa Monica Fwy; San Diego Fwy; Hollywood Fwy; Ventura Fwy; etc.

In Las Vegas, you have the Boulder Highway, which points towards Boulder City.

I'm thinking this is much more of an eastern US phenomenon because most city streets were laid out much more haphazardly before the mid 1800s, and a road simply connected two cities the best way possible. Once you got past the Mississippi River, towns were laid out more in grid patterns.

[KCRoadFan]

A bunch in New England, Kentucky, and Georgia.

Toledo Road on the east side of Elkhart, Indiana (former US 20).

Somewhat closer to home: Kansas City Road in the suburb of Olathe, Kansas.

[Rothman]

A bunch in New England, Kentucky, and Georgia.

"A bunch" in New England is an understatement, as I implied above.  Just in MA alone, practically every town has a road named for a neighboring town that switches names at the township border.

[GenExpwy]

Somewhat odd, here in Wayland NY: Lackawanna Street (NY 15 and part of NY 21), which runs due north-south. North is toward Springwater and Rochester, south is toward Hornell (21) or Cohocton/Bath/Corning (15). Lackawanna NY is to the west-northwest, next to Buffalo.

Where the street did go in the old days was the local station of the Delaware, Lackawanna and Western Railroad. So in that sense only, it was the way to Lackawanna.

[Coelacanth]

In the Twin Cities:
Hudson Road
Wayzata Blvd
Stillwater Blvd
Minnetonka Blvd
Rockford Rd
White Bear Ave
Excelsior Blvd
Plymouth Rd

Osseo Rd
Golden Valley Rd
Stillwater Ave/Rd in addition to Blvd above
Centerville Road

[cpzilliacus]

Not only is this very common, but in some places the road's name will change when you cross county lines to refer to the town you just left. For example, Dirt Roads mentions the Durham area in North Carolina. Roxboro Road (US-501) is so named because Roxboro is the next town to the north. It's in the next county over. When you cross the county line, suddenly you're on Durham Road.

U.S. 1 south of Washington, D.C. is Richmond Highway in several sections (and also Jefferson Davis Highway though that name is becoming disfavored)

U.S. 1 north of Washington is Rhode Island Avenue (an extension of its D.C. name), then Baltimore Avenue north to the north edge of Laurel, then Washington Boulevard most of the way to Baltimore.  Then Southwestern Boulevard then Wilkens Avenue.  Headed north from Baltimore, U.S, 1 is Belair Road starting in the city and keeps that name most of the way to Bel Air.  Approaching Bel Air, Belair Road turns off onto Business U.S. 1 as it gets close to Bel Air suddenly becomes Baltimore Pike.

For added fun, U.S. 1 becomes Conowingo Road (probably in honor of the town that disappeared beneath the waves of the reservoir created when Conowingo Dam was built across the Susquehanna River) north of Bel Air.

[webny99]

It's somewhat common in NY for a road to be named for the towns it connects... Walworth-Ontario Road, for example.

NY 31 is also named Rochester Rd heading east out of Lockport, but it has various other names before it actually gets to Rochester.

[Evan_Th]

U.S. 1 north of Washington is Rhode Island Avenue (an extension of its D.C. name), then Baltimore Avenue north to the north edge of Laurel, then Washington Boulevard most of the way to Baltimore.  Then Southwestern Boulevard then Wilkens Avenue.  Headed north from Baltimore, U.S, 1 is Belair Road starting in the city and keeps that name most of the way to Bel Air.  Approaching Bel Air, Belair Road turns off onto Business U.S. 1 as it gets close to Bel Air suddenly becomes Baltimore Pike.

Rhode Island Avenue sort of counts for this thread too, since US 1 does eventually go to Rhode Island!

[hobsini2]

Naperville, IL has a number of these types of streets.
Chicago Ave
Aurora Ave
North Aurora Rd
Plainfield-Naperville Rd
Naperville-Wheaton Rd
Warrenville Rd
Oswego Rd

I did find a Warner map of Naperville from 1870 online. According to that, Aurora Ave was High St and Chicago Ave was Water St.