Solution
Let the two means be $\mu_x$ and $\mu_y$ and their standard deviations be $\sigma_x$ and $\sigma_y$, respectively. The difference in timings between two rides ($Y-X$) therefore has mean $\mu_y - \mu_x$ and standard deviation $\sqrt{\sigma_x^2 + \sigma_y^2}$. The standardized difference ("z score") is
$$z = \frac{\mu_y - \mu_x}{\sqrt{\sigma_x^2 + \sigma_y^2}}.$$
Unless your ride times have strange distributions, the chance that ride $Y$ takes longer than ride $X$ is approximately the Normal cumulative distribution, $\Phi$, evaluated at $z$.
Computation
You can work this probability out on one of your rides because you already have estimates of $\mu_x$ etc. :-). For this purpose it's easy to memorize a few key values of $\Phi$: $\Phi(0) = .5 = 1/2$, $\Phi(-1) \approx 0.16 \approx 1/6$, $\Phi(-2) \approx 0.022 \approx 1/40$, and $\Phi(-3) \approx 0.0013 \approx 1/750$. (The approximation may be poor for $|z|$ much larger than $2$, but knowing $\Phi(-3)$ helps with the interpolation.) In conjunction with $\Phi(z) = 1 - \Phi(-z)$ and a bit of interpolation, you can quickly estimate the probability to one significant figure, which is more than precise enough given the nature of the problem and the data.
Example
Suppose route $X$ takes 30 minutes with a standard deviation of 6 minutes and route $Y$ takes 36 minutes with a standard deviation of 8 minutes. With enough data covering a wide range of conditions, the histograms of your data might eventually approximate these:

(These are probability density functions for Gamma(25, 30/25) and Gamma (20, 36/20) variables. Observe that they are decidedly skewed to the right, as one would expect for ride times.)
Then
$$\mu_x = 30, \quad \mu_y = 36, \quad \sigma_x = 6, \quad \sigma_y = 8.$$
Whence
$$z = \frac{36 - 30}{\sqrt{6^2 + 8^2}} = 0.6.$$
We have
$$\Phi(0) = 0.5; \quad \Phi(1) = 1 - \Phi(-1) \approx 1 - 0.16 = 0.84.$$
We therefore estimate the answer is 0.6 of the way between 0.5 and 0.84: 0.5 + 0.6*(0.84 - 0.5) = approximately 0.70. (The correct but overly precise value for the Normal distribution is 0.73.)
There's about a 70% chance that route $Y$ will take longer than route $X$. Doing this calculation in your head will take your mind off the next hill. :-)
(The correct probability for the histograms shown is 72%, even though neither is Normal: this illustrates the scope and utility of the Normal approximation for the difference in trip times.)