Westbrook, Gorham + Windham

Neighboring Portland and Sebago Lake, these three communities invite you to explore their historical downtowns, culinary offerings, and outdoor recreational opportunities.



PineCrest Inn is a short walk from Gorham’s downtown, which will make exploring the town easy. My friend, Zach, and I have reservations at MK Kitchen, so I walk over after checking in to my room. The restaurant is laid- back but stylish, with a thoughtful menu from chef-owner Mitchell Kaldrovich that highlights his range. Kaldrovich is known for his delicate lobster cones, but we opt to start with duck liver pâté and a plate of local cheeses. Zach’s entree is a decadent duck confit cassoulet, while I order the special: seafood paella with squid, shrimp, and mussels.



I start my day with a run through downtown, past the University of Southern Maine, and along Route 114’s sloping hills. I have plans to meet friends in Westbrook, so I grab a quick breakfast at a longtime southern Maine institution, Mister Bagel.

I follow the Westbrook River Walk trail that runs alongside the Presumpscot River behind downtown. The trail is a little over a mile long and provides views of the river and mill buildings that were powered by its water. My friend Cat Bates, a jeweler and metalsmith, has a studio in the Dana Warp Mill, a former textile mill that has been converted into offices, artist studios, and other commercial spaces. I find his door after a few wrong turns down long, cavernous hallways. After showing me around his high-ceilinged studio, he demonstrates a sand casting of one of his necklaces. After hammering a mold of sand, he melts a piece of bronze, then pours in the molten metal to create the piece, a rugged yet elegant design that he’ll finish with a nylon cord.


We head over to Mast Landing Brewing Company after Cat cleans up to grab lunch and sample a few beers. I order a Rachel sandwich from Kind Stack Sandwich Co., which is serving food in the tasting room, before picking out some beers. Opened in 2015, Mast Landing has perfected the popular, hazy New England–IPA style and offers a range of other styles, including a surprisingly not-too-sweet peanut-butter milk stout called Gunner’s Daughter.

In the center of downtown near the start of the Westbrook River Walk is Black Dinah Chocolatiers’ factory and storefront. Kate and Steve Shaffer first opened the confectionery company in 2007 on Isle au Haut before moving operations to Westbrook three years ago. Steve gives me a tour of the production facility, including a station where Kate is sending squares of caramels down a conveyor belt that leads to a curtain of chocolate. Before leaving, I buy two handfuls worth of chocolate, including ancho chile bark, a bark with Maine sea salt and roasted pecans, and assorted truffles, as Christmas stocking stuffers for my girlfriend and other family members.


Zach meets me for dinner in Gorham again, this time at Sebago Brewing Company. The brewery also has brewpubs in Scarborough, Portland, and Kennebunk. A new brewery facility, which will also include a tasting room and restaurant, will open in the new year, east of downtown on Main Street. You can’t go wrong ordering a burger here, and I go with the Imperial, with cheddar, a fried egg, bacon, and chipotle aioli. Zach’s shepherd’s pie is generously sized and includes 100 percent grass-fed beef. Bonfire Rye is my favorite of Sebago’s regular beers, so I have a couple pints of this hoppy rye ale.



The Frog and Turtle’s Sunday brunch is a popular destination for locals. Unlike most brunch spots in Portland, you can make reservations here. The gastropub’s brunch menu features standard breakfast fare, including several options of eggs Benedict, but what really shines is the house-made doughnuts. They’re made from scratch and fried to order, and you can choose the toppings and fillings.

After a filling breakfast, I head to Mill Brook Preserve for some outdoor exploring. The Presumpscot Regional Land Trust owns this 130- acre nature preserve in Westbrook. The preserve has about five miles of trails, which follow Mill Brook between Route 302 and Methodist Road. Sections of the trail near the middle are more difficult, but the entire route offers scenic views of the brook. During late May and early June, alewives can be seen migrating upstream. Snow is covering the trail today, but the well-marked trees make it easy to stay on the trail.


Driving to Windham next, I stop at Babb’s Bridge, a covered bridge that connects Windham and Gorham over the Presumpscot River. The original Babb’s Bridge was built in the mid-1800s, but vandals burned it down in 1973. The state built a replica of the bridge and reopened it to traffic in 1976. There are rope swings located on the shore of the Gorham side.