Gorham, Westbrook + Windham

Located between Portland and Sebago Lake, these Cumberland County communities each offer a unique experience, from artisans working in a repurposed Westbrook mill to newcomer MK Kitchen anchoring Gorham’s downtown to Windham’s natural beauty.


5:00 p.m. @ PineCrest Inn, Gorham

My fiance, Adam, and I check in with the help of Amy Mattingly, who owns the inn with her husband, Matt. She suggests a few spots around the inn to check out. Our king bedroom suite with its own adjoining bathroom is stunning.

6:00 p.m. @ Sebago Brewing Company, Gorham

This brewpub, popular among both locals and tourists, also has locations in Portland, Scarborough, and Kennebunk. Adam and I decide on the potato nachos, burgers, and a buffalo chicken salad.

7:15 p.m. @ iSpoon, Gorham

This fun establishment has self-serve frozen yogurt that you can mix and match and then pile with an assortment of toppings. We feel like kids here, and our eyes are most definitely bigger than our stomachs. After we enjoy our treats, we decide to call it a night.

8:00 p.m. @ PineCrest Inn

We return to see that Matt and Amy have left Lindt chocolates on our pillows. We couldn’t feel more at home. We brew some decaf coffee and settle in—we have a big day planned tomorrow.


8:30 a.m. @ PineCrest Inn

Matt and Amy no longer run a restaurant at the inn, but they still serve breakfast. We enjoy the delicious breakfast sandwiches Matt makes for us with fresh fruit.

10:00 a.m. @ Westbrook River Walk

We pick up my mom on our way to the trail that follows the bank of the Presumpscot River to the mill buildings and downtown. It is a nice way to start our morning, as we scope out where we should start our day.

10:45 a.m. @ Black Dinah Chocolatiers, Westbrook

We decide that we should treat ourselves to chocolate first. We walk in and meet the owner, Kate Shaffer. She is fabulous, friendly, and down to earth. My mom and I love the beautiful designs that Kate and her team have created—the artistry is impeccable. We sample a strawberry balsamic chocolate that is surprising and delightful. We leave with an array of bars to share: coffee peanut, ancho chile, and almond sea salt.

11:30a.m. @ Don’s Lunch Van, Westbrook

If you’re in Westbrook, you should stop here. The van is dressed up in fun colors. We decide on burgers, fries, and chicken tenders to split.

12:15 p.m. @ The Baker’s Bench, Westbrook

The Baker’s Bench is a suggestion from my aunt, who has been a Westbrook resident for the past 20 years. This bakery and sandwich shop is busy, and the dessert cases are brimming with raspberry brownies, éclairs, scones, cupcakes, and peanut butter pies. We seek out the perfect treat for after dinner.

12:45 p.m. @ Windham Jewelers

We meet Kaylee Ayers upon entering, and she assists my mother with her purchase and questions. I browse the beautiful selection of estate jewelry, watches, rings, and so much more.

1:15 p.m. @ Half Moon Antiques, Windham

This shop is really cute, and we take some time exploring the restored and repainted pieces to get ideas for our own homes.

1:45 p.m. @ Babb’s Bridge, Windham/Westbrook

Located on Hurricane Road, the covered bridge connects Windham and Westbrook over the Presumpscot River. I climb down some makeshift steps leading to the water. When I reach the last rock I see rope swings some local kids have attached at the bottom of the bridge. This is a great resting spot before we head back to Gorham.

3:00 p.m. @ PineCrest Inn

We decide to go back to the inn to show my mom our room. She loves it and now wants everyone who comes to visit to stay here.

 3:45 p.m. @ The Gorham Grind

This coffee shop in downtown Gorham is just what I need before dinner. The tables are topped with maps of different countries, and one of the chairs is the kind you see in a hair salon. The coffee is sourced from Coffee By Design, and I get a cup of the Jazzy Java blend.

5:00 p.m. @ MK Kitchen, Gorham

My mom and I decide to have a dinner date while Adam goes back to the inn. MK Kitchen’s decor is classy and elegant. Lisa Kaldrovich, who owns the restaurant with her husband, chef Mitchell Kaldrovich, greets us and directs us to the bar for a drink while we wait for the kitchen to open. Once we’re seated at our table by the window, we order our entrees: gnocchi mac and cheese for me and a vegan quinoa bowl for my mom. Both dishes are both beautifully prepared and exceed our expectations.

7:15 p.m. @ PineCrest Inn

After a long day, I head back to our room to see Adam. We discuss our favorite parts of the day and dive into the treats from the Baker’s Bench.


9:30 a.m. @ The Frog and Turtle, Westbrook
We meet up with my parents at the Frog and Turtle, which is well known for its brunch, especially
the doughnuts. We order four and understand why. The doughnuts are freshly made and hot. The Elvis, filled with chocolate, peanut butter, and banana, is divine. The pretzel doughnut is sweet and salty—a perfect way to start our morning.

12:30 p.m. @ Erin Flett’s design studio, Westbrook

We have an appointment to meet designer Erin Flett at her studio in the Dana Warp Mill. She tells us about her process and shows us some of the hand-screened textiles and woven fabrics she designed. After we leave, I keep raving to Adam about the designs and end up shopping on her Etsy site later in the day.

1:30 p.m. on the road

We loved being able to discover so many fun places so close to home. We start discussing when we’ll head back to relive our amazing weekend.