Skip to Content

How to Spend a Day in Windham, Maine

How to Spend a Day in Windham, Maine

How to Spend a Day in Windham, Maine

Windham, Maine, has often been described as a drive-through town. It’s the gateway to the Sebago Lakes Region and one of the last places to stock up before getting to your destination.

People say they drive through Windham to get somewhere else. However, if you miss Windham, you’ll miss some enjoyable activities, fun shops, and boundless places to grab an excellent bite to eat. 

Let’s explore Windham!

About Windham, Maine

Windham was incorporated in 1762, well before Maine became a state in 1820. And, as a matter of fact, there are a lot of relics leftover from some of Windham’s early years. Some of these include the Cumberland and Oxford Canal, the gunpowder mill at Gambo Falls, and the Mountain Division Trail. The latter follows the old Maine Central Railroad tracks, which are used for recreation now.

Thirty minutes from downtown Portland, Windham has a population of close to 20,000 people, many of whom commute into the larger city for work.

The historical society in Windham is very active. They’re building a community green surrounded by many of the town’s old buildings, such as the South Windham Library and a schoolhouse.

Windham’s weather can vary from -21 degrees on a cold January day up to 100 degrees on a summer scorcher. Those extremes are rare, but they do happen. That said, the best time to visit Windham is between June and September.

The town’s main road is US Route 302, which will take you all the way into the White Mountains of New Hampshire. Windham borders Sebago Lake, the deepest lake in Maine, where Portland and surrounding towns get their public drinking water. In addition, the lake water reaches an average temperature in the seventies most summers.

Presumpscot River by Paul Noble Photography on Flickr

Morning in Windham, Maine

Breakfast at Chute’s Family Restaurant

Address – 686 Roosevelt Trail, Windham.

Chute’s serves both breakfast and lunch, making it the perfect place to start your day. And, don’t miss the treats from Lisa’s Bakery Case, such as the giant cinnamon buns.

They have unique items on the menu like Hunters Hash, containing shaved steak, home fries, peppers, onions, mushrooms, tomatoes, and topped with cheddar cheese.

Or try the Fish Hash made with haddock, home fries, onions, and cheddar cheese. There are also specials depending on the season, and all of the bread is homemade. Lunch provides a wide variety of soups, salads, and hot or cold sandwiches.

Chute’s opened in 1978. After a short stint without a Chute at the helm, Maila Chute returned with her family to Maine and purchased the Windham location to continue the family tradition.

Visit Dundee Park

Next, spend the morning swimming at Dundee Park on the banks of the Presumpscot River. This park is a great place to cool off and relax while never leaving town.

The park is run by Windham Parks and Recreation and has ball courts and boat rentals, and a roped-off swimming area with lifeguards on duty.

There are picnic tables, and in the summer, they have a concert in the park Wednesday evenings. Dundee Park does have an entrance fee.    

Image Source: Bob Travis on Flickr

Afternoon in Windham, Maine

Eat lunch at Rose’s Italian Restaurant

Address – 690 Roosevelt Trail, Windham, just up the street from Chute’s.

The menu here is traditional Italian fare, with old standards thrown in to appease the pickiest eaters. (Chicken fingers, anyone?)

Although, the best reason to eat at Rose’s is the wood-burning brick oven pizza. Feel free to create your own or try one of their creations.

Regardless, the crispy crust on the outside and chewy goodness inside will make you consider coming back for dinner.

Rose’s has a laid-back atmosphere with scents that will tempt your tastebuds. Most importantly, remember to pick up a dessert to take home.

Go Kayaking or Paddleboarding

Sebago Trails Paddling Company is run by a father and daughter who want to make sure everyone can get out on the water. The shop is located just a few miles outside Windham, Maine, on Route 302 in Raymond. They have their own private launch onto Sebago Lake. Whether you like sit-in kayaks, sit-on-top kayaks, canoes, or paddleboards, you can rent one at Sebago Trails Paddling Company.

Just learning? Sebago Trails can make sure you know what to do and how to do it safely before you get out on the water. You can purchase boats on site. If you’re staying nearby, you can rent a kayak, paddleboard, or canoe and have it dropped off at your location for the week.

Before You Go: Not sure if you want to rent a kayak or a canoe? We can help you figure it out.

Take Time for Some Self Care at Heaven and Earth Day Spa

Address: 108 Tandberg Trail, Windham.

Heaven and Earth Day Spa and Wellness Center is a haven for those with sore muscles or who need a little pampering after a long day exploring, driving, or paddleboarding. They have a variety of services, from facials and waxing to massage and body treatments. And they do recommend reservations.

Soft music, dim lights, and a professional massage therapist relaxing your body and mind…it truly is heaven on earth.

Evening in Windham, Maine

Dinner at Elbow Room Bistro

Address – 781 Roosevelt Trail (Route 302), Windham.

The bistro is touted as “chef-inspired cuisine.” The chefs take traditional food and give it a twist or some extra spice. One of the most popular items is the Ramen Bowl.

The menu is compact but has a little something for everyone. For example, some of the items on the menu are sandwiches like bacon cheeseburgers or turkey clubs. Other offerings include grilled chicken or sirloin steak and salads – Greek, Chef, or Caesar – all with homemade dressings.

This is a small location with atmosphere to spare. It’s a niche restaurant like you’d find in Portland but in the heart of Downtown Windham. All the reviews rave about the food.

Drinks at Erik’s Church

Address – 824 Roosevelt Trail, Windham, tucked in the back of the strip mall.

The menu contains pub fare with five dinner entrees like meatloaf, mac and cheese, and pulled pork. Not in the mood for another dinner? Try appetizers like poutine or buffalo chicken dip. If you stay long enough, you might want to try a pizza or one of their burgers.

Nightly country or local bands, a dance floor, and a fully stocked bar make it a great evening stop. They even put on a karaoke night and make sure the music never stops.

Take a shooting class at Windham Indoor Shooting Range

Address – 999 Roosevelt Trail, Windham

For the novice shooter or the seasoned veteran, Windham Indoor Shooting Range offers a wide variety of classes and experiences for everyone. Introductory classes and concealed carry classes are offered regularly. In addition, the store allows rentals of firearms for the classes.

You can also rent and try out firearms when booking a lane on the range. If you have a firearm, you’re welcome to bring it for practice and they have ammunition for purchase. The range recommends reservations for both classes and range time. The motto of WISR is “Training starts at the door.” 

Where to stay in Windham, Maine

Family & Friends Campground

Address – 140 Richville Road, Standish, about 10 minutes outside of Windham.

This 70-site privately-owned campground is a lovely oasis. Amenities include a pool, hot tubs, playground, and fishing pond. There are activities on the weekends for all.  

This is certainly a family campground with lots of kids playing on the playground and riding bikes on the roads. Activities are based around theme weekends such as candle making, rain gutter regattas, or crafts like tie-dying.

Spending Your Day in Windham

There are so many more things to do in Windham, Maine. If you drive through to Sebago Lake or the White Mountains without stopping, you’re missing out on history, cuisine, and exciting places to walk, hike, and paddle. Stock up on everything from music and books to hardware and RV supplies. You can find it all in Windham.

Discover the Best Free Camping Across the USA

To be honest with you, we hate paying for camping. There are so many free campsites in America (with complete privacy).

You should give it a try!

As a matter of fact, these free campsites are yours. Every time you pay federal taxes, you’re contributing to these lands.

Become a FREE CAMPING INSIDER and join the 100,000 campers that love to score the best site! 

We’ll send you the 50 Best Free Campsites in the USA (one per state). Access the list by submitting your email below:

%d bloggers like this: