There are several places to enter the carriage road and run the Day Mountain loop. For this particular ride, I started at the entrance to Wildwood Stables – there is a small parking area just after you turn onto the Stanley Brook road to park your car. It is a nice trip with great views as you loop around the mountain. The trip to the summit is well worth the energy, and you can stop for a hike to see Day Mountain Caves. The summit is a great place to have lunch, and enjoy the downhill ride back. Note that in the heart of summer this loop is heavily traveled by horse and carriage from the stables and can become a little bumpy and you’ll be dodging horse poop, but still worth the ride!