This trail is located in Raymond Maine, about 45 minutes outside of Portland. Because the Raymond/Windham area has such a large volume of traffic, I would definitely recommend doing this hike either on a weeknight or very early in the morning. That way, you won’t get stuck in a sea of boats, jet skis, trailers, and large trucks. Trust me, it will make your experience much more enjoyable.

This trail is located in Raymond Community Forest, which is maintained by Echo Land Trust. They are also responsible for maintaining one of my other favorite mountains in Southern Maine called Bald Pate. You can click here to read more about that hike. The trailhead is located right off of Raymond Hill Road (also known as route 85) in Raymond. If you’re coming from Portland, Google Maps will most likely take you right up Route 302 until you meet up with route 85. After you turn right on Route 85 North, you will turn onto Raymond Hill Road, follow that for three miles, and then turn left onto Conesca Road for 0.8 miles, and the parking lot will be on your left.

This trail has a nice large, dirt parking lot. I definitely don’t think parking is anything to be concerned about, which is a nice change of pace. At the trailhead, you will find a map of all the trails, as well as free printed maps. There was signage that indicated ATV’s were not allowed. Dogs are allowed, on leash. From the parking lot, the first trail you come to is the Spiller Homestead Loop, where you can either go right or left. If you go left and then straight, you will be completing the Spiller Homestead Loop, a 1.1 mile trail that loops back to the parking lot and also meets up with the Pismere Bluff Trail, which takes you to the summit. If you take a left and then a right, you will be completing the Grape Expectations Trail, which is a 1.1 mile trail that meets back up with the Spiller Homestead Loop Trail, giving you the option to return to the parking lot or to continue on to the Pismere Bluff Trail.

I chose to take the Spiller Homestead Loop Trail to the Pismere Bluff Trail, because it was a very hot day and I wanted to summit early before it got too hot. To get to the Pismere Bluff Trail from the Spiller Homestead Loop, you will have to cross the road. Do so cautiously, as a lot of cars tend to haul ass down that road.

Once you cross the road, you will come across some boulders and a small grassy field. Keep going through the field, and you will slowly find yourself submerged in the woods. Then, the trail quickly inclines as you make your way up the mountain. I was huffin’ and puffin’ quite a bit on this trail, which was great. It’s hard to find a hiking trail in Southern Maine that actually makes you feel like you got a good workout in. Another great feature of this trail are some man-made rock steps. I always love when a trail has rock steps, it just adds something special.

The Pismere Bluff Trail is about 0.7 miles long and will eventually bring you to a four-way intersection. Going either right or straight will bring you on the Highlands Loop Trail, a nice 0.7 mile loop trail. I decided to veer left at this intersection and check out the summit. The summit provided fantastic views of surrounding lakes and mountains, especially Crescent Lake. It’s an exceptional spot to take a break and eat a snack or lunch.

After spending some time at the summit, I decided to head back to the four-way intersection and explore the Highlands Loop Trail. I’m glad I did. It was well-maintained, quiet, and shaded. After completing that loop, I headed back down the Pismere Bluff Trail and then returned to the parking lot. Normally, I would have also added the Spiller Homestead and Grape Expectations Loop Trails to the end of my hike, but it was very hot outside and I hadn’t packed a lunch, so I decided to play it safe and go home.

I would highly recommend this hike to anyone looking for a fun, moderate, dog-friendly, family-friendly hike in Southern Maine. I would actually go so far as to say that this hike is one of my top 3 hikes in Southern Maine. Why? Because it’s within an hour of Portland, is very quiet and secluded, and provides great views for not a lot of work. Oh, and it automatically gets five stars because of how dog-friendly it is.

Happy hiking, friends!