Getting There: From Rapid City, SD travel south on Sheridan Lake Road/Old State Highway 40 (paved road) for 8 miles until you reach Victoria Lake Road (a well-maintained gravel road).
There are no signs identifying the start off the trail and, in general, there are very minimal markers along the trail.
Parking: You can park at a pull-out right off Highway 40 and ride your bike 0.2 miles down Victoria Lake road to another parking area right at the start of the connector trail. There are large boulders placed at the start of the connector trail.
To get to the start of the Victoria Lake Lollipop Ride, take the connector trail from the parking area down to the Victoria Lake Loop 15
trail which is the trail you are on for the majority of the Victoria Lake Lollipop Ride. From the parking lot, travel through the boulders 20 yards on a doubletrack then take the unmarked singletrack that branches left into the trees (this is the start of the connector trail). Follow a short ravine down to a long narrow meadow. At the end of the meadow, the connector trail from the parking lot meets with the Victoria Lake Loop 15
trail. To start the Victoria Lake Lollipop Ride, take a left at the intersection and head southwest. You'll start climbing gradually, traveling south up a ravine filled with a mixture of pine and deciduous trees.
On your way out, the stem of the lollipop is 90% climbing. It has switchbacks that make it doable, but it is a workout. Locals call the climb from the start to about 1/4 of the way around the head of the lollipop the "Lollipop Climb" or "The Big Climb." The difficult climbing on your way out has brief technical sections, but you are aptly rewarded by the flowy downhill on your way back.
The intersection marking the start of the head of the lollipop is in an open area of the forest. At this intersection, you get off of the Victoria Lake Loop 15
trail. There is a small yellow sign with a black directional arrow mounted on a stump at about ground level. Most riders ride the head of the lollipop counter-clockwise, but it is also fun clockwise. Just after leaving the intersection to start the head of the lollipop, you'll see where the trail crosses a dirt logging road and heads back into the trees (there is a brown trail marker that states "no motorized vehicles." The first 1/4th of the head of the lollipop is a serious climb with occasional 15+ inch obstacles to test your technical skills and leg power. Once you are approximately 1/4th of the way around the head of the lollipop you have finished "The Big Climb." Cross another dirt logging road at another brown trail marker stating "no motorized vehicles." Approximately half of a mile past that brown trail marker you'll come to an unmarked intersection. Stay to the left at the intersection to continue on the Victoria Lake Lollipop ride. If you want to tackle more trail take a right to get on the Extra Credit Connector
to add an extension loop that connects you to the Victoria Lake Loop 15
trail further west. If you are just doing the head of the Victoria Lake Lollipop stay to the left as instructed above, and in approximately 20 feet you'll come to another unmarked intersection that connects you back to the Victoria Lake Loop 15
trail. Take a left at this intersection getting back on the Victoria Lake Loop 15
trail. Now you can settle into the downhill with sections of flowy singletrack around the rest of the head of the lollipop and back down the "stem" to the parking area.