This is a fun question - I don't know of a huge data set but some ideas I had for generating one are:
Strava API
If you have a free API key, you can query Strava's segments end point and give it a lat/lng boundary, so you will get start and end points within those bounds (but limited to 10 results so you'd have to loop to get enough data and may exceed your API call limit, however if you just create it once it might not be so bad). You could also get a lot of points from a specific bike ride/run, but they'd all be close together which I don't think you want.
http://strava.github.io/api/v3/segments/#explore e.g.
Throttling
The default rate limit allows 600 requests every 15 minutes, with up
to 30,000 requests per day.
API call
curl -G https://www.strava.com/api/v3/segments/explore \
-H "Authorization: Bearer YOUR_TOKEN" \
-d bounds=37.821362,-122.505373,37.842038,-122.465977 \
Response
{
"segments": [
{
"id": 229781,
"name": "Hawk Hill",
"climb_category": 1,
"climb_category_desc": "4",
"avg_grade": 5.7,
"start_latlng": [
37.8331119,
-122.4834356
],
"end_latlng": [
37.8280722,
-122.4981393
],
"elev_difference": 152.8,
"distance": 2684.8,
"points": "}g|eFnm@n@Op@VJr@"
},
{
"id": 632535,
"name": "Hawk Hill Upper Conzelman to Summit",
"climb_category": 0,
"climb_category_desc": "NC",
"avg_grade": 8.10913,
"start_latlng": [
37.8334451,
-122.4941994
],
"end_latlng": [
37.8281297,
-122.4980005
],
"elev_difference": 67.29200000000003,
"distance": 829.834,
"points": "_j|eFvc@p@SbAu@h@Qn@?RTDH"
}
]
}
Google Geocoding API
This API will accept an address and give you a lat/lng (and more) but is throttled. You'd just need a list of addresses which would be pretty easy to get.
API https://developers.google.com/maps/documentation/geocoding/
Throttling
Users of the free API: 2,500 requests per 24 hour period. 5 requests
per second.
API call
https://maps.googleapis.com/maps/api/geocode/json?address=1600+Amphitheatre+Parkway,+Mountain+View,+CA
Response
{
"results" : [
{
"address_components" : [
{
"long_name" : "1600",
"short_name" : "1600",
"types" : [ "street_number" ]
},
{
"long_name" : "Amphitheatre Pkwy",
"short_name" : "Amphitheatre Pkwy",
"types" : [ "route" ]
},
{
"long_name" : "Mountain View",
"short_name" : "Mountain View",
"types" : [ "locality", "political" ]
},
{
"long_name" : "Santa Clara",
"short_name" : "Santa Clara",
"types" : [ "administrative_area_level_2", "political" ]
},
{
"long_name" : "California",
"short_name" : "CA",
"types" : [ "administrative_area_level_1", "political" ]
},
{
"long_name" : "United States",
"short_name" : "US",
"types" : [ "country", "political" ]
},
{
"long_name" : "94043",
"short_name" : "94043",
"types" : [ "postal_code" ]
}
],
"formatted_address" : "1600 Amphitheatre Pkwy, Mountain View, CA 94043, USA",
"geometry" : {
"location" : {
"lat" : 37.42291810,
"lng" : -122.08542120
},
"location_type" : "ROOFTOP",
"viewport" : {
"northeast" : {
"lat" : 37.42426708029149,
"lng" : -122.0840722197085
},
"southwest" : {
"lat" : 37.42156911970850,
"lng" : -122.0867701802915
}
}
},
"types" : [ "street_address" ]
}
],
"status" : "OK"
}