Historical sites, museums, local restaurants, coffee shops, boutiques, and many outdoor adventures await you at Windham.
Located in Cumberland County in Maine, Windham is the namesake for Wymondham, a market town in South Norfolk, England.
First settled by farmers in the early 1700s, the town wasn’t considered safe because of the wars between French and Native American Indians.
Today, Windham prides itself on its rich history and culture, which are kept alive by its historical society.
Lounge and relax in one of its restaurants downtown, sip a delicious cup of coffee, or get your pulses active at a shooting range.
Anything is possible in town for adventure-seekers like you.
For a more guided trip, here are the best things to do in Windham, Maine:
Pass by the Historic Parson Smith House
Parson Peter Thatcher Smith, the town’s second minister, built the Parson Smith House in 1764.
The historic house remained a private home for many decades until 1952, when it was turned into a museum by the Historic New England Society.
In 1973, the house museum was added to the National Register of Historic Places.
The museum was open to the public until 1991, when it was sold to new ownership, and remains a private residence to this day.
However, the new owner signed an agreement upon purchase that there would be no interior and exterior changes to be made in the house.
The Parson Smith House was one of Maine’s first Colonial Georgian architecture.
Since it’s now a private home, there might be no chance to see its interiors, but tourists passing by will have a good view of the house from the main road.
It’s nestled on River Road on an elevated site in southern Windham.
Stay at Microtel Inn & Suites by Wyndham
Comfort and easy access come in handy at Microtel Inn & Suites by Wyndham, established in 2015.
Staying here allows you to take advantage of its heated indoor pool and free continental breakfast.
Feel at home in their comfortable beds and clean sheets, and enjoy its modern amenities while getting around.
Conveniently nestled on Roosevelt Trail, Microtel Inn & Suites by Wyndham is only a few minutes away from downtown and Windham’s top tourist attractions.
Enjoy a Full Day of Fun at Seacoast Adventure
For action-packed adventures on your trip to Windham, Seacoast Adventure has a lot of things in store for you!
During the summer season, you can enjoy playing mini-golf and go-karting.
It also features a Shipwreck Cove Water Playground, specially built for kids, where they can have fun at the plunging buckets, slides, and bubblers.
If you want to feel the thrill of skydiving, you can try the 100 feet Sky Swing, which is popular in Windham!
In the winter, snow tubing also awaits you.
They have an in-house restaurant called Deck House Tavern with many delicious dishes.
Everything is fun and exciting at Seacoast Adventure with your family and friends.
Visit them at Route 302 on Roosevelt Trail.
Step into the Past with Windham Historical Society
The historic town of Windham offers vast insight into its past.
Founded in 1967, the Windham Historical Society preserves the town’s history and culture to keep them alive over time.
It maintains the historic Old Town Hall, which served as the Town Meeting House, office, and school in the past.
The society also maintains the Old Grocery, the Old Windham Library, the October House, and many other historical architectures.
You can find Windham Historical Society on Windham Center Road.
Hike up the Sebago to the Sea Trail
One of Maine's quietest and uncrowded trails is the Sebago to the Sea Trail, where you can spend peaceful afternoon hikes.
The scenic views stretch from the town of Standish through Gorham, Windham, Westbrook, and Falmouth to the Portland sea.
In Windham, you can start exploring on Main Street.
Whether you wanna go for a run, hike, or bike ride, the Sebago to the Sea Trail offers beautiful views of the water.
The trail was established in 2007.
Have a Bite of Pizza at Portland Pie Company
Are you looking for the best pizza in town?
You can have it at Portland Pie Company with its delicious pizza pies in different flavors!
It also offers a gluten-free crust for those with food restrictions.
Choose from its different dough flavors, such as beer, garlic, wheat, and basil.
What’s more exciting is that you can build your own pizza, perfect for vegans or vegetarians.
Vegan cheese, vegan- and vegetarian-friendly toppings, and vegan protein are also available.
Portland Pie Company is located on Roosevelt Trail.
Shop for Gifts and Souvenirs at The Craft Shop
Whether you’re traveling alone or with your family and friends, you can’t miss a stop at a beautiful gift shop.
At The Craft Shop, you’ll find nice, perfect gifts and souvenirs you can take home with you.
Everything pretty is available here, from scented candles, handmade soaps, antiques, home decor, woodwork, and weaving supplies to greeting cards.
The Craft Shop will fascinate you with every treasure you can find.
Established in 1992, this eclectic gift shop is located on Roosevelt Trail in downtown Windham.
Activate Your Pulses at Windham Indoor Shooting Range & Retail Store
Are you after a different kind of action-packed adventure?
Keep your pulses ready to shoot at Windham Indoor Shooting Range & Retail Store.
If you’re into guns, this would be your perfect place as it offers a lot of stuff for firearms.
They have handguns, rifles, ammo, and many more.
The facility has a state-of-the-art indoor shooting range where you can spend a few hours shooting and keeping your pulses active.
If you’re a first-timer, they also offer training and classes about guns, how to shoot, and everything about firearm safety.
Windham Indoor Shooting Range & Retail Store was established in 2015 and claims to be the biggest one yet in southern Maine.
You can find it on Roosevelt Trail.
Get Pampered at Freedom Massage & Wellness
Spend an hour or two at Freedom Massage & Wellness to experience a relaxing massage in a comfortable setting with calming music in the background.
Their hot stone massage and deep tissue massage are to die for!
They also offer lash extensions, waxing, and more beauty treatments.
In addition, the spa sells essential oils, lotions, and nice jewelry in the reception area.
A warm and cozy atmosphere awaits you at Freedom Massage & Wellness.
You can find it downtown Windham on Roosevelt Trail 11.
Watch a New Release at Smitty’s Cinema Windham
If you’re up for a movie day or night at Windham, head to Smitty’s Cinema Windham to see new releases in a more relaxed setting.
The theater features lounge chairs with long tables where you can eat your favorite snack while watching a movie.
It’s not a traditional movie theater, which is why locals and tourists love it.
Its surround sound is great, and the food is decent.
Overall, the setting would be like you’re in an office, but you’re watching a movie on a bigger screen!
That’s more fun, right?
Smitty’s Cinema Windham is located on Roosevelt Trail.
Hike and Picnic at Donnabeth Lippman Park
On a sunny afternoon, you can take scenic walks around Donnabeth Lippman Park.
The beautiful wooded area of the park makes a great location for hiking along the Chaffin Pond, where there’s a 10-acre area for fishing.
The picnic tables and benches on the trailhead are great for picnicking while enjoying the beautiful views.
The park also features playground equipment for the kids to enjoy.
Formerly known as Chaffin Pond Preserve, Donnabeth Lippman Park is a 123-acre wooded area with trails for hiking and nature viewing.
You will also see different species of birds at the park, making sightseeing more fun.
The park is located at Chaffin Pond Road.
Grab Your Favorite Coffee at Aroma Joe’s
How about a cup of your favorite coffee to kickstart your day in Windham?
Whether you want to stay for a little while or grab one and get around downtown, Aroma Joe’s makes it easier.
The coffee shop offers handcrafted coffee with unique, delicious flavor mixes to enjoy while taking advantage of its warm and relaxing atmosphere.
It also offers cold drinks, espresso, and baked products like donuts, muffins, cookies, and brownies.
Even the kids can enjoy the coffee shop’s hot and cold chocolate drinks!
Aroma Joe’s is located on Roosevelt Trail.
Drop by Windham Hill United Church of Christ
Windham Hill United Church of Christ was one of the town’s first local churches when its name was changed to Windham.
The church was built in 1835 with little to no changes, and also the first one to have a bell.
Its interiors still have the same vaulted ceilings, box pews, white plastered walls, and beams.
Some of the church’s old footstools and collection boxes remain in use.
An Italianate steeple was added in 1885, which was repaired in 1990.
In 1924, a beautiful stained-glass window was also added to the church.
You can find the historic Windham Hill United Church of Christ on Windham Center Road.
Other Things to Do Nearby
As beautiful as Windham, its neighboring towns also offer one of the best tourist attractions in Maine.
These spots are only a few minutes from Windham, so if you get past the border, get ready for another great experience!
See the Historic Babb’s Covered Bridge
The historic Babb’s Covered Bridge spans the Presumpscot River and connects the towns of Windham and Gorham on Hurricane Road.
It’s said that it was built as early as 1840 and was named after a family who settled nearby.
In 1972, the bridge was then listed on the National Register of Historic Places.
However, in 1973, the covered bridge was destroyed by arson.
In 1976, a new replica was dedicated through the joint efforts of Gorham and Windham Historical Societies.
The bridge was one of the 10 covered bridges in Maine before its destruction, which pushed many volunteers to build a replica instead of a new modern type of bridge.
Babb’s Covered Bridge has been one of the most popular tourist attractions in both Windham and Gorham towns.
It’s only seven minutes away from downtown Windham via Chute Road and River Road.
Taste the Maine Wine at Cellardoor Winery
Inspired by a hobo a hundred years ago, Cellardoor Winery produces wines in a warm and welcoming environment.
Two of its popular vintages are Blanc de Blancs and Bulles Rose, which you should try when you’re here.
Cellardoor Winery Portland, in 2018, was the first to produce Maine’s first Ice Wine.
It’s only 24 minutes away from Windham on Middle Road in Portland.
The hobo symbol carved on its door is worth the visit!
Windham is one of Maine’s gems with a rich history that remains alive to this day.
It’s filled with beautiful tourist attractions to share with your friends and loved ones.
Pack up, experience the town’s unrivaled beauty, and enjoy the best things to do in Windham, Maine!