The Perfect Weekend in Maine
By Morgan Rizzo
Planning a visit to Kennebunkport off season? There’s something quite special about visiting this quaint Maine coastal town after Labor Day when the rush of summer fades. Maybe it’s the natural beauty of the foliage reflecting in the water as a sailboat drifts by, or maybe it’s the quieter streets lined with pumpkins on door steps and a refreshing pumpkin beer waiting at the local restaurant. Either way, a fall getaway to Kennebunkport, Maine is the perfect escape.
Where to Stay
Checking into the historic Breakwater Inn transports visitors to a coastal retreat. The inn, newly renovated, overlooks the harbor where the Kennebunk River meets the Atlantic ocean, giving guests a glimpse into Maine’s coastal heritage.
Its Waterside Cottage is a must stay, adding privacy for a romantic weekend. Turning the buoy keychain and stepping inside, natural light floods the room through floor to ceiling windows overlooking boats docked on their moorings. The open-concept room offers a master bed, living room, kitchen and the bathroom of a guest’s dreams with the extra perk of heated floors. As the sun slowly sets over the horizon, the Waterside Cottage takes on a fiery glow and the best panoramic view. Opening the doors lets the salty ocean breeze flow through the room making it hard to leave the room to explore the town and a sad Sunday morning having to depart.
From the historic photos of sailboats to the coastal color palettes of the room, every detail exhibits maritime charm. The recent renovations created nautical elegance with its unmatched views, modern comfort and design.
It’s backyard offers the best view of sunset with Adirondack chairs perfect for an afternoon relaxing with a glass of bubbly wine in hand. A visitor favorite is the Oyster Mary and mini charcuterie board on their happy hour menu. Grab one of the complimentary bicycles to ride into town to visit art galleries and upscale boutiques while making sure to eat at the inn’s sister restaurants including Kport Provisions, Bob’s Clam Hut, and Mabel’s Lobster Claw, a favorite of Matha Stweart and others.
Where to Eat
A quick walk away is the Breakwater Inn’s new dining venue, the Port Fish & Chop House. There’s nothing quite like sipping on an espresso martini on the outdoor patio watching boats including guided tours make their way across the river.
Open for dinner, guests are greeted with a dining room filled with chatter and laughter. In one room, patterns of book shelves lined the walls while a chandelier glistened from the ceiling.
Starting with a bottle of Pinot Noir off their curated wine list is a fantastic start to a delicious dinner from the chefs. Staff favorites include the burrata with tomato and balsamic drizzle offering a fresh start to the meal along with the shrimp al ajillo. With a crispy chili flake, the shrimp has just the right spicy bite to it. For the main course, selections include both local seafood and fine cuts of meat. The pan roasted halibut with mashed potatoes, glazed carrots and beurre blanc is the perfect meal for a chilly fall night. And, it’s necessary to try one of their Chop House steaks; the rib-eye with a side of mac and cheese won’t leave diners disappointed. Finish off the evening with the turtle cheesecake.
Aside from the Port Fish & Chop House, a few other local spots stand out. Grab a pretzel with beer cheese and DownEast Cider at Batson River Brewing & Distilling in Kennebunk. Brewed Awakenings in Wells, Maine has a seasonal fluffy pumpkin latte and the “Morning Glory” breakfast sandwich is their take on a breakfast BLT. For late night margaritas and birria tacos, Treehouse Taqueria in Ogunquit is the best stop and only a short drive away. Where historic shipyards built schooners, Federal Jack’s, one of Maine’s first brew pubs has a tasty specialty fall martini, pecan pie.
What to Do
First things first, stroll through the downtown. With the leaves beginning to change colors, and pumpkins, gourds and vibrant mums sitting in antique truck beds Kennebunkport fully embraces the fall season. Stop at all the fall photo opps along the way.
October offers crisp mornings and evenings with warmer afternoons ideal for strolling along the shops and grabbing fall cocktails and food along the way. From shops for a touristy sweatshirt with a red lobster stitched on the front to local fudge, travelers can find the perfect souvenir to take home with them at the Dock Square Emporium and The Candy Man.
The Knotty Elephant is a children’s store inspired by family history with a performing group of elephants. For everything from autographs of Yankees’ baseball players and panoramic photographs of Fenway Park to antiques, one can spend hours looking throughout the collections of the Stadium Gallery.
Even without a clear agenda in mind, from the small downtown area to the scenic shoreline, Kennebunkport makes an easy fall getaway for all travelers. If you’re looking for more coastal inspiration, check out our guide to the best East Coast beach towns.
