Stunning Off-The-Beaten Path Maine Hikes You’ve Never Hit
An Adventure Up the Coast of Maine from Portland to Vinalhaven Island
A long weekend adventure with a starting point in Portland, Maine has a lot of options, but for Memorial Day weekend, my partner, Jack and I decided to plot our way up through Maine’s MidCoast & Islands. Driving no more than an hour at a time, our trip felt effortless, letting us focus on the adventures ahead rather than the getting there. Friday morning we grabbed our coffees and hit the road. Three days, the perfect long weekend trip up the Coast of Maine. We each made a video to share our experiences:
So you can follow along with our adventure, this was our route from Portland.
Day 1
First stop: Devil’s Back Trail in Harpswell, Maine. Devil’s Back trail offered a beautiful introduction to our weekend. Easy-to-find trailhead, ample parking, and well-marked trails impressed us right away. After following some short switchbacks through the rocky woods, we arrived at the quintessential Maine oceanscape. Rocky coastline, sunshine, salty air. The perfect lunch spot.
Our next stop was the Sebasco Harbor Resort, in Phippsburg, Maine where we were greeted by kind and helpful staff and a beautiful room, overlooking a beautiful campus. We explored their lighthouse, grabbed an ice cream cone at their little shop, and roamed around the grounds discovering beautiful details everywhere we looked.
From the resort, we headed back to Harpswell for a hike of Cliff Trail during golden hour. The 90-foot cliff views overlooking the water were stunning. It was so unexpected! I had no idea a hike like this existed so close to Portland. I’ll be back for this one.
Day 2
After a restful night at Sebasco Harbor Resort, we woke up early to sounds of rain on the balcony outside. Some rain gear and an 8 minute drive landed us at the Wilbur Preserve at Cox Head trail. The trail was pristine, and we didn’t cross paths with anyone but birds and frogs the whole way to the top. Once we got there, we were greeted by a view that felt almost like an observation tower. Getting to look down on these coastal towns and islands, far from the city was such a treat.
Expecting more rain, we decided to take refuge in Downtown Boothbay Harbor on our way to our next hike. Delicious breakfast burritos and hot coffee at The Red Cup Coffeehouse fueled us while we let our raincoats dry off. It was a bustling but welcoming spot to be while it came down outside. When the rain cleared for a moment, we took a walk around the harbor.
A quick and scenic drive took us to Oven’s Mouth Preserve in Boothbay, another coastal trail system I’d never heard of before. When we got out of the car we noticed a fellow Mainer hauling clamdigging gear out of his car. He headed for the ocean, and we headed for the woods. The trails zig-zagged through the woods to the ocean and each turn showed us a new perspective of the water. One turn gave us the most Maine image I’d ever taken: our clamdigging acquaintance, trudging through the marsh, buckets in both hands, while the mist filled-in around him. This entire hike was stunning. Although it was raining a little, with it brought this beautiful hovering fog over the water, and each inlet along the hike provided incredible views.
Ready to dry off and get cozy, we made our way to Ocean Gate Resort in Southport, Maine. As soon as we got there, we were welcomed in by the resort’s owners who gave us the rundown on the place. They’re such enthusiastic and kind people who clearly value and understand hospitality. We parked in front of our cabin and grabbed our bags, only for our jaws to hit the floor when we walked inside and saw the view from the balcony. Wall to wall windows framed vast ocean views through tall pine trees. Exploring the grounds was equally stunning. Around the docks we actually saw little jellyfish swimming around! This was a place we really didn’t want to leave.
That night, the sunset over the fog was incredible. These are views from our evening walk and from our cabin’s balcony:
Day 3
Finally, on Sunday, we embarked on our journey to Vinalhaven Island. Stopping at the terminal in Rockland, we grabbed our bikes and some tickets and boarded the ferry. The hour-long ferry ride was half the fun! As we got closer to Vinalhaven, we passed through lots of little islands, each perfectly picturesque. With the sun out again, we enjoyed the breeze on the top deck and rested our legs.
Once on the island we immediately jumped on the bikes and hit the road, only to be distracted right away by Lawson’s Quarry. This spot was such a gem, and we will definitely be back to swim in it’s crystal clear water. it was so quiet and peaceful, clean, and beautiful. We spent the rest of our time cruising around the island, almost every driver that passed by waved to us.
On the ferry ride back to conclude our trip, I leaned back into my seat and reflected a bit on everything we fit into this wonderful weekend in Maine. It was almost too easy to have a vacation-worthy time, and with this collection of off-the-beaten-path hikes, we were able to discover a lot more than we could have ever prepared for. After experiencing all of these unexpected sights and sounds, I can only imagine what else is hiding in MidCoast that we haven’t discovered yet.
Again, here’s the map of our route. We also made a Google Map link of the entire getaway for anyone inspired to take a similar road trip.
Sarah McLean and Jack Stolz are a Portland, Maine-based couple focused on sharing their adventures through video, photos, and storytelling. With backgrounds in graphic design and music, the two put a creative spin on travel, exploring the outdoors, and discovering new experiences right “in their backyard.”
