Maine Winter Running Challenge: Part I
I’m always looking for ways to spice up my training and make our occasionally monotonous sport just a little more interesting. Though I find a lot of joy in running itself, sometimes I need a bit of extra incentive or challenge to keep the hours fun—especially this time of year, when the majority of my miles take place in the sub-freezing darkness.
Enter the Maine Winter Running Challenge. At the end of the fall, I set out to discover more of the beautiful state I’m fortunate to call home through running. The rules of this self-created “challenge” were pretty simple—Each week (ish), I’d choose a different town and run at least a marathon distance through it, exploring new trails and roads while holding myself accountable to putting in the miles during a season when motivation often lacks.
Maine has well over 400 towns and cities, and I certainly don’t intend to get to all of them. I began this challenge with no specific goal in mind, but after some thought, I think at least 26 would be a good minimum number to shoot for. 26 marathons (or more) through 26 different towns sounds pretty cool, right? When designing routes, I’ve been pretty strict about staying within the chosen town boundaries—no cutting into a neighboring town for the sake of running a nice loop! I also finish most sessions by stopping at a new coffee shop or bakery. Because why not.
I’m now 10 towns deep into the effort, and thought I’d highlight my top 10 favorite trails and routes I’ve explored thus far (some of which I was already familiar with, others that were new). Maine is such a gorgeous state, and though our trails may not receive quite as much hype as the neighboring White Mountains or Adirondacks, there are certainly a few hidden gems. Not to mention the general beauty that running around here features—many local roads truly feel like traveling into a postcard. To anyone living in or venturing to Maine, hopefully this will give you a few ideas for some new routes, trails, and adventures!
Towns run so far: Falmouth, Wells, York, Kennebunk, Harpswell, Yarmouth, Cape Elizabeth, Phippsburg, Freeport, & Georgetown
#10 - York Beaches (Long Sands, Short Sands, & Nubble Lighthouse)
York is my pick for the all-around best town for running in the state. Sitting just north of the New Hampshire border, it features stunning beaches, trails of all character, and a small mountain with an auto road that I’ve done many an exhausting workout on.
The beaches of York can’t be beat. My favorite runs here involve parking at Short Sands Beach, running along Nubble Road past the lighthouse, and turning left onto Long Beach Ave for a long, flat stretch of stunning ocean views. Other days, I’ll run in the opposite direction down Shore Road towards Ogunquit for a more rolling route. Either (or both!) ways, the views are absolutely incredible.
Where to eat: When in York, I always stop by Anthony’s Food Shop post run. I have yet to find a better breakfast pizza. They also have a full bakery & coffee menu, smoothie bowls, and breakfast/lunch sandwiches.
#9 - West Side Trail (Yarmouth)
The West Side Trail is a 10-ish mile out-and-back beginning in the coastal town of Yarmouth and weaving through forested singletrack before crossing a bridge to Cousins Island and continuing down the trails there. This was one of my first FKTs (there’s an FKT for the standard out-and-back and one for 3 times out and back for a 50k), and a route I love to run in all seasons. The island is easily the highlight of this run.
Where to eat: Cuppa Jo is the cutest little coffee/bakery stop. I love the English muffins. Clayton’s Cafe is another great spot for breakfast, lunch, coffee, & baked goods. It’s always bustling, but for good reason!
#8 - Laudholm Farms (Wells)
The gentle trails of Laudholm Farms are always peaceful and gorgeous. Though they aren’t extensive, I love running a loop of winding singletrack past the marsh and then connecting to nearby Drake’s Island and the beach.
Where to eat: Bake Maine, a little cafe right off of Route 1, has the best homemade biscuits and a nice breakfast/lunch/drink menu. For a traditional sit-down diner, it doesn’t get much better than the Maine Diner.
#7 - Mt. Agamenticus auto road & surrounding trails (York)
Mt. Agamenticus is a little peak (only 692 feet!) with a nice trail network surrounding it, and an auto road featuring a Strava segment with some wicked fast times. There’s a 50k held here each May (which was, coincidentally, my first ever ultra) that features 3x10.35 mile loops on the trails, and the course is a great route for training runs.
#6 - Moody Beach (Wells)
As one of the most popular tourist destinations in the state, Wells has quite a few gorgeous stretches of beach. My favorite route in town involves running along Ocean Avenue, where you’re steps away from the water the entire time. Bonus if it’s the off-season—Wells becomes a ghost town after the leaf-peepers drive south, and that’s absolutely the best time for exploring.
#5 - Cape Elizabeth roads & greenbelt trails
I’m biased (Cape is my home turf), but I think most would agree my town is one of the most beautiful in the state if not the world. The roads are quiet and scenic, a small network of trails runs through the town, and you can’t go more than a few miles without stumbling upon a beach.
A few favorite runs in Cape Elizabeth include the famous Beach to Beacon 10k course, the Cross Town Trail (side note - I did an internship with the town Land Trust in high school and helped create this trail guide!), and Fort Williams Park. Cape Elizabeth is one of those extremely runner-friendly towns where you can run for miles without worrying about busy road crossings or tons of traffic combined with narrow shoulders. I’ll forever be grateful to have grown up in a town that makes space for and celebrates runners.
Where to eat: C Salt Gourmet Market has the world’s best breakfast sandwiches, and it doesn’t get any better than their homemade English muffins.
#4 - York Water District Trails
The York Water District Trails are the best kept secret in Southern Maine. I’ve run for hours without seeing another person. The miles and miles of rolling single-and-doubletrack will make you feel like you’re deep in the woods, when you’re never more than a few minutes from a road or backyard. Park at Mt. Agamenticus for easy access.
#3 - Morse Mountain (Phippsburg)
Morse Mountain is a hidden gem in the lower Midcoast Maine town of Phippsburg. The climb up, which is more of a dirt road than a trail, is short and sweet, and when you descend the other side you end up at one of the most beautiful beaches I’ve ever seen. I had never run here before, and it felt like stumbling upon a secret island. Phippsburg in general is a stunner—from Popham Beach State Park, to Hermit Island Campground, to the many oceanside roads.
#2 - Kennebunk Bridle Path & downtown
The entire town of Kennebunk (and neighboring Kennebunkport) is straight out of a postcard, whether you’re running the 5.6-mile Bridle Path, cruising past the ocean on Beach Avenue, or glimpsing the Bush’s summer retreat on Walker’s Point. There aren’t many hills in Kennebunk (for better or for worse), so it’s great for flat, fast workouts. Don’t miss Cape Porpoise, a village in Kennebunkport, either.
Where to eat: Dock Square Coffeehouse in downtown Kennebunkport! Best lattes and (clearly) pumpkin bread!
#1 - Cliff Trail & Bailey Island (Harpswell)
I’m trying to come up with different ways to express the beauty of running in Maine, but in the end, you just have to be here to experience it. Running down Harpswell Islands Road over the bridge into Bailey Island is like a dream. There are a handful of trails that I’ve yet to explore around here, but the Cliff Trail is a lovely little loop, with some challenging scramble-y sections mixed in with gentle dirt doubletrack.
Where to eat: Dog Bar Jim in nearby Brunswick has an excellent menu and always has the best specials!
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And that’s it! I realize that all of my towns thus far have been on the southern coast of the state (hence the ocean/beach theme of many of these!) but I hope to explore some different areas of the state as my schedule allows.
The state of Maine should sponsor you. What a fun way to tour (and share) your state 👌🏼