Most trail write-ups treat Monument Hill as a quick out-and-back with a nice view. That framing misses what it actually is for people who live in Leeds. The hill is short enough that it isn't the day; it's the piece that lets you build a day. Twenty minutes up, a picnic table under a pine, and you are back at your car with the whole afternoon still ahead of you, sitting inside a fifteen-mile radius of two of the oldest working orchards in Maine.
That is the thesis of this post. Monument Hill isn't a hike you drive to. It's the anchor that stitches together a Leeds fall Saturday.
What "going up Monument Hill" actually means
There are two marked routes from the North Road trailhead, and locals don't use them interchangeably. Both the yellow and red routes are equally short at roughly half a mile, and the yellow trail is slightly easier. Tripadvisor reviewers refer to the same routes as the Orange and Red trails, both of which go to the summit and can be linked as a loop. Either way, the round trip lands at about 0.9 miles with 183 feet of elevation gain, and most people finish in half an hour to an hour.
The reason locals pay attention to which trail they pick is what waits at the top. The red trail turns a bit ledgy before reaching the summit clearing, where a flag pole stands with the monument, and the far western ledge holds a picnic table positioned under a pine to take in the view. There are at least four picnic tables on the trail system: two at the top, one near the top on the red trail, and one halfway up. That picnic table on the western ledge is the reason to bring a thermos. On a clear day the summit offers partial views with Mount Washington visible when visibility cooperates.
If you have kids in tow, the yellow side is the friendlier climb. If you have out-of-town guests you want to impress in under an hour, take the red side up for the ledge sequence and come down yellow.
The monument itself is not what visitors assume
Here is where most write-ups get lazy. They call it "a Civil War monument" and move on. The people who put it there were very deliberate that it wasn't that.
The obelisk was erected in 1895 by Major General Oliver Otis Howard, who was from Leeds. Howard was appointed commissioner of the Freedmen's Bureau, where he oversaw the integration of formerly enslaved people into American society, and he helped found Howard University in Washington, DC. The idea came from his family. Distinguished natives of Leeds, Major General Oliver Otis Howard, Rev. Rowland Bailey Howard, and Brigadier General Charles H. Howard, were all involved in the idea and erection of the monument to final peace marking the end of the Civil War.
Howard was specific about what the monument was for. In the kiosk text at the trailhead, he is quoted saying it was not meant to praise "the peace cause in general," but rather was to specifically commemorate "the peace triumph of 1865…bringing, as we trust, a lasting, perhaps an everlasting, peace to our country."
That framing matters when you are standing next to it with your coffee. This is the highest point in Leeds, and the town that lost more people per capita to the war than any other town in Maine chose to mark the end of the fighting rather than the fighting itself. Leeds had the largest per capita number of people serving in the war of any town in the State of Maine. Once you know that, the obelisk reads differently.
The Saturday loop that only makes sense from Leeds
Here is the geometry that makes Monument Hill the anchor rather than the destination. Inside a short drive of the North Road pullout sit two working orchards on very different rhythms, and pairing them with a summit picnic gives you a full day without doubling back.
Ricker Hill Orchards, Turner. Fifteen minutes west. The family has been growing apples, pumpkins, Christmas trees and more on the farm since 1803, which puts it into its ninth generation. Hours are generous: March and April 8 to 5, May through October 8 to 6, November and December 8 to 5. On the property you can string together apple picking, fresh maple donuts with a glass of homemade hard cider, breakfast, and a round of disc golf. It functions less like an orchard stop and more like a small campus.
Boothby's Orchard & Farm, Livermore. Twenty minutes north. Two addresses to keep straight. The seasonal farm market sits at 1425 Federal Road on Route 4 and is open late June through October featuring fresh fruits and vegetables, grass-fed beef and wine, as well as a bakery co-op with breads and baked goods from other local farms and artisans. The pick-your-own orchard at 366 Boothby Road on Route 108 runs on a tighter window: open September through Columbus Day, Thursdays through Sundays 10 to 5. In 2026 the market opened mid-June with a Thursdays to Sundays, 10 to 5 schedule and free wagon rides on Sundays.
The point isn't to list orchards. The point is that these two are on different clocks and offer different things. Ricker Hill is open every day and heavy on activity. Boothby's is Thursday-through-Sunday, quieter, and built around the wine tasting and pick-your-own. A Leeds resident who knows both can pick the right one for the mood of the morning.
Here is the sequence that works: leave the house at 8:30, park on North Road by 9, up-and-over the loop with coffee at the ledge picnic table by 9:45, back to the car by 10:15, and at whichever orchard fits the day by 10:45. You are home by early afternoon with cider donuts on the counter and boots still muddy by the door.
Small things that separate residents from weekend visitors
A few details that don't appear in the top-ten Google results but shape how locals actually use the hill.
- The pullout is small. There is no parking lot at the trailhead, just a minuscule pull-off beside the road. On a foliage Saturday it fills. Arriving before ten is not overkill; it's how you avoid parking on a shoulder curve.
- The bugs are real until the ledges dry. Reviewers repeat this in every season. Challenges include mosquitoes, mud, and some elevation. Bring bug spray and check for ticks after hiking. September onward is when the hill stops fighting you.
- Carry it out. There aren't any trash receptacles, so we need to play our part in keeping the area clean. The picnic tables are only useful because nobody trashes them.
- The flag needs friends. A longtime local visitor noted on the trail listing that someone does need to take better care of the flag put up there because it looks pretty ragged at times. If you are the kind of person who notices, the Leeds Historical Society is who to talk to; they run the Jane's Walk ME summer program on this trail.
- The return trail is not marked. The return trail leaves from the granite overlook and is not marked. Do not follow the big yellow arrow at the turn off to the monument, which will take you to the wrong side of the hill. Come down the way you went up unless you know the loop.
Why this matters if you already live here
You could drive to Bradbury or Streaked Mountain for a longer day, and plenty of people do. What Leeds has that those don't is a summit inside town lines with two working orchards inside a twenty-minute radius on complementary schedules. That is a fall routine, not a hike. The people who moved to Leeds in the last few years and are still treating Monument Hill as a "someday, when guests come" errand are missing the actual best use of it, which is the fifteen-Saturday stretch from Labor Day through late October when the ledges dry, the bugs quit, the apples run, and the western view opens up between leaves.
The obelisk has been up there since 1895. It will still be there next weekend. The window on the loop that surrounds it is shorter than that.
If you live around Leeds, Greene, Turner, or Livermore and you are starting to think about what a home here should actually give you back, that is a conversation worth having over coffee. Integrity Homes Real Estate Group knows this stretch of Central Maine the way locals know which trail dries first, and we would rather help you find a Saturday routine than sell you a floor plan. Book a Free Home Consultation whenever it suits you.
