A Perfect Fall Family Adventure on Blue Hill Peninsula
48 hours of cottages, hikes and incredible scenery… with none of the Summer crowds
“It was such a perfect weekend. It didn’t feel overly kid oriented but the kids enjoyed all of it. The natural beauty was off the charts and it’s really nice to know you can visit here in the off season. It’s very easy to fill a 3-day weekend; great pace to things, great food, absolutely beautiful location. A weekend in the Blue Hill Peninsula leaves you wanting to stay for longer.”
The Blue Hill Peninsula, a 1 hour drive from Bangor and a 2.5-hour drive from Portland, delivers an idyllic blend of natural beauty, family-friendly hikes, and delectable cuisine. From coffee shops to candy shops, the Blue Hill region and Deer Isle have everything you need to slow down for a weekend and enjoy time together. Making the trip in the Fall, as the leaves begin to turn, gives visitors a picturesque backdrop for the weekend while the tourist crowds remain notably absent. The Blue Hill Peninsula is the ideal locale for a family retreat, one that even the youngest travelers can savor through manageable hikes and peaceful moments.
Pro Tip: Check Blue Hill Heritage Trust Events Calendar for any family friendly activities to incorporate into your trip.
Day 1: Settling into Deer Isle
Start by checking yourself into one of the comfortable cottages at the historic Pilgrim’s Inn. The main inn building was built in 1793 as a private residence and in 1890 it first welcomed guests as an inn. The owners are incredibly gracious and the surrounding natural beauty makes this the perfect homebase for a weekend exploring the Blue Hill Peninsula. After you’re unloaded, head over to Mariners Memorial Park to stretch your legs.
This beautiful little park on the water is just 5 minutes away from the inn and it feels like a secret spot that only the locals know.
By now the vacation vibes should have officially set in; the bridges, forested road corridors and ocean views make for an almost magical drive to dinner. We recommend the modern Brooklin Inn Restaurant in Brooklin for adult and kid-friendly dinner. They hit all the right notes with the excellent service, great food and a contemporary vibe. The burger and hand cut fries are a classic; finished with their chocolate dessert.
Dinner at Brooklin Inn Restaurant
Day 2: Blue Hill Mountain and Brooklin
We started Saturday with breakfast at Pilgrim’s Inn; sourdough toast with goat cheese, eggs and arugula & french toast for the kids. Follow this up with a coffee at 44 North Coffee, just a few doors down. Apart from excellent coffee, they feature a wraparound porch with views of the Northwest Harbor cove; close enough that the kids can hound for sea glass while the parents sip coffee.
Morning at Pilgrim’s Inn
Pro Tip: Forgot your nighttime books or looking for something new to read? Stop by the Chase Emmerson Memorial Library on your way back to the inn.
For your late-morning adventure, grab a picnic blanket and then plan to hike the Blue Hill Mountain Loop. Stock up for a picnic lunch atop the mountain by stopping at the Blue Hill Farmer’s Market (open Saturdays, 9:00am to 11:30am from May through October). Apple cider donuts were in season, we also grabbed some carrots, cheese and crackers. If you’re looking to spend more time in Blue Hill, check out Blue Hill Books, Bucklyn Coffee, Horton Emerson Park, and Blue Hill Coop.
The moderately difficult hike is about 2 miles round trip and will take around 1.3 hours. Our 5 year old was able to tackle the stone steps on his own and we found snakes, grasshoppers, several species of birds as well as wild berries on our way up. The top of Blue Hill Mountain is phenomenal, large granite slabs with views of the islands including the MDI (Mt Desert Island, home to Acadia National Park). Find a nook among the stone and trees to picnic and take in the view before a leisurely hike down.
Atop Blue Hill Mountain
The afternoon found us back in Brooklin with a pizza and soft-serve lunch at Brooklin General Store. This is a classic general store with a gracious owner who opened up his soft serve ice cream shop for us. Next door, Leaf & Anna is a small shop stocked full with gifts, toys, puzzles and more. No visit to Brooklin would be complete without stopping at Brooklin Candy Co. This curated candy shop is “nostalgia to the nth degree,” featuring throwback candies and something for every taste. It’s so good; you have to stop whether you’ve brought kids with you or not.
Must stop: the Brooklin Candy Store
If you’re in the mood for an afternoon adventure, check out the Hundred Acre Wood Trail then have an early dinner at Strong Brewing & Kitchen. Their meatball subs or wood fire pizzas are incredible and, of course, pair it with a pint of Maine beer. For a full list of hikes, trails, playgrounds and a neat hand-drawn map, check out this Healthy Peninsula in Blue Hill document.
We stopped back at our cabin and then took the short drive down to Stonington for dinner at Fin and Fern. Ask for a seat upstairs which gives you a private setting with panoramic views of downtown Stonington and the coast. This intimate restaurant feels both high-end while also being welcoming to children. Order any of their fresh seafood; we went with halibut, fish and chips and a pizza.
After dinner at Fin & Fern
Day 3: Mossy Preserve and a Railroad Ride
If you’re an early-bird and the weather is nice, try taking a sunrise swim at Sylvester’s Cove. Or wake up the old fashioned way with another great breakfast at Pilgrim’s Inn. They change it up daily; this time it was a Mexican-inspired breakfast with great coffee.
Peering off the back deck of Ragusa Rose, the cottage at Pilgrim’s Inn
After breakfast we went to Barred Island Preserve for an otherworldly hike that was easy for the entire family. You’ll walk amidst lush green moss, a vibrant and fresh fragrance fills the air, accompanied by the sweet scent of beech trees. The path leads to granite mounds that give way to crystal clear water; at low tide you can walk out to Barred Island itself. For help identifying the flora, check out a virtual guided nature walk by the Island Heritage Trust.
The coastal trails, unique sandbar access, and moss-carpeted forest make Barred Island Preserve a truly special part of the Downeast Acadia region.
Nearby, Aragosta at Goose Cove offers an ocean front dining with a spectacular view. Stop by for lunch and/or visit their gift shop which offers highly curated, ocean-inspired items.
To finish out the weekend we drove up to Ellsworth for the DownEast Scenic Railroad Ride. On the way, stop by the walkup coffee counter at Bucklyn Coffee in Blue Hill. There will likely be a line of locals and it’s worth the wait! In Ellsworth, stop by Helen’s Restaurant for lunch and if time allows, take a stroll through the Stanwood Wildlife Sanctuary.
The DownEast Scenic Railroad is a 12-mile round-trip ride in restored passenger train that’s perfect for families with young kids. The conductor was super friendly, some staff were dressed as pirates and the free pick-your-own-pumpkins were a nice pre-Halloween touch.
