That's my philosophy as well. But with the bulk of the city to the west and north, a big lake to the south, and a prevailing westerly/southwesterly wind, it doesn't often work that way.

My usual trails have a slight grade to them, so I battle the grade more than the wind, but a headwind when going down grade does suck some of the fun out of it.

I tend to do out & back rides, starting the hard direction, and cruising back... so I understand the feeling.

Also, one of my favorite trails has a bike rental company that also provides a shuttle service that will bring me back to the car for $19.95 (or a season pass for $99, which I have) so I can ride 10-36 miles down and get a ride back. Those are my most pleasant rides. Well worth the $5-10 per ride I willl end up paying by the end of the year.

How long is the typical wait for a ride back?

They actually leave on a schedule, only a couple of times in the afternoon, so I time my riding to coincide with their schedule (giving myself a little extra time).

However, if I get there and have time to kill, it is in the wonderful little town of Jim Thorpe, with several nice shops, galleries, bars and cafes... and even a mansion tour I haven't taken yet, or the jail house I haven't visited yet where some of the Molly Maguires were hanged... (not all history is pleasant)

Depending on timing and my desire, I can do the shuttle from the bottom of the trail to bring me to one of 3 points further up the trail I want to ride from, and then ride down. If I do that, my car will be waiting for me.

I typically do the ride/shuttle when I don't have anything pressing to do on a weekend/holiday.

Dude!
Whatever spins your wheels!
Most fun ride of my life was with a 50-ish mile tailwind... Passing cars in a 55 mph zone!

Ride back sucked, ended up pushing and going the long way to get SOME wind break...

<just used Sheldons gear calc, at most I was doing about 36... Funny felt faster at the time! passing must have been due to the storm...>

@ 75, you can do whatever works for you.

+1

I rarely have a choice, given that most of my rides are group rides and the route decider is someone else. But my preference is to take the tailwind first. If you know it's a tailwind, you can plan your exertions accordingly; but who knows??? The wind could always shift and give you tailwind on the way back, too.

Headwind on the return trip? This is what the small chainring is for.

Before any ride of about thirty-forty miles or more, I always check the wind forecast and plan my ride accordingly. The wind out here in the high desert is pretty persistent/reliable as to its direction. Velocities are all over the gauge, but usually lighter in the mornings and intensifying in the afternoons as the thermal currents become stronger.

The best web site I've found for wind forecasts is actually a web site designed for ultra-light, radio control, para-glider, and other small aircraft.

Air Sports Net - News and Weather for Aviation Pilots

Click on "Weather" in the menu bar along the top, and select "Aviation Weather". In "Get Locations", select your state from the "Select a Region" pull down menu. Press "Go". Then in the "Get Forecast", select the nearest location to you from the "Select a Location" pull down menu. Again, press "Go".

The locations seem to be airports or other weather stations. It gives a two and a half day forecast in three-hour time chunks. Below is the current forecast for my area. For winds like are being forecast, looks like I'll be heading west on the outbound leg, and enjoy a nice boost on the way home. These are conditions for setting PRs on Strava.

What is this "small chainring" of which you speak?

These hipsters today got nuthin over the track bikes back in the day.