15 Best Things to Do in Waterboro (Maine)

Waterboro is a small city of around 7,000 people, located in the York County of Maine. The town includes multiple lakes, so was initially known as Massabesic, which translates into “the place of much water” in the Abenaki language.

The land was first bought by Major William Phillips in 1661 and later passed to his heirs and other proprietors. One of them was Colonel Joshua Waters, the man who inspired the final name of the city.

Waterboro was incorporated as a town in 1790 and its economy was based on lumber, agriculture and dairy farms.

When in Waterboro you can:

1. Hike to the Ossipee Hill Summit

This is a great, family-friendly hike that will take you through the woods and up to the top of Ossipee Hill. Besides the usual activities such as hiking, mountain biking, running or walking the dog, you can also ride an ATV on this trail.

The hike is easy to handle and it’s not that long; the view at the top is pleasant. If the season is right, you will also find plenty of blueberries to pick.

Some people suggest that you can get the best view by climbing on the old fire tower, but we don’t recommend doing this since the tower is old and abandoned.

2. Have lunch at Woody’s Sports Grille

Woody’s Sports Grille is one of the best eating spots in Waterboro; some people even claim that they have the best burgers in New England

It’s a warm and friendly place with lots of tasty meals to choose from. Besides the famous burgers, you can also find great wings, fries, nachos, salads, sandwiches, steaks, seafood and more.

For dessert, you can get a luscious cheesecake or a delicious peanut butter pie.

3. Have fun at Little Ossipee Lake

In spite of its name, the lake is not overly small. It spreads over a large surface and is quite deep. It is inhabited by loons, bald eagles and other types of birds, as well as multiple species of fish.

The lake is a great place for fishing, whether you are an experienced angler or just want to give it a go. There are plenty of water sports and activities on offer, including boating and jet skiing.

There is also a camping ground nearby. Overall, the lake is clean and well preserved.

4. Stroll through Goodall Park

If you happen to be in the area on a lovely summer’s day, head to this park; it has plenty of beautiful alleys and benches, as well as a playground for the kids.

You will also find a baseball field and basketball court. If there’s a game going on, feel free to go and take a look. You might be lucky enough to see the Sanford Mainers baseball team in action.

This is a clean, safe park to spend a nice afternoon with the kids or the dog.

5. Have a beer at the Funky Bow Brewery

What better way to quench your thirst after a long walk in the park than with a cold beer. You can find a great brew or two at the Funky Bow Brewery & Beer Company.

There are plenty of beer assortments to choose from, as well as pizza and other snacks. But what really sets this place apart from other breweries are the staff, who go out of their way to ensure you have a good time.

There is often a live band performing, so you can sip on your amber ale while listening to some great music.

6. Visit the Alfred Shaker Museum

The Shakers were a thriving community many years ago in the nearby city of Alfred. The first member of the family who arrived here was a musician, but in time, they expanded into art, furniture, design, agriculture and many more fields.

Today, this museum located in a barn hosts a large collection of tools, crafts, photos and clothes that used to belong to members of the Shaker community. It’s a great attraction for history buffs.

The museum also offers lectures, craft shows, events and workshops for both locals and tourists.

7. Visit the Seashore Trolley Museum

Located nearby in the city of Kennebunkport, this museum is the largest one in the world that features an electric railway. Among the many interesting exhibits, you will find old trains, trolleys, trams, buses and more.

It’s a great location for the entire family; you can easily spend a few hours here wandering around admiring the machinery and taking lots of photos. You can even take a ride in some antique rail cars.

8. Relax at Parsons Beach

Found in Kennebunk (which is connected to the Atlantic Ocean), this is a lovely beach and a popular tourist attraction. Here, you can lie back on the sand and get a tan, go for a swim, or just wander along the shore.

The beach is large enough to hold hundreds of people and is clean and well maintained. It is usually quiet; there are no parties or noisy crowds.

Overall, it’s a charming place to spend the afternoon if it’s a warm, sunny day.

9. Pick berries at Joan & Brad’s Berry Farm

This is a small, family-run blueberry farm which offers visitors the chance to pick their own fruits and pay by the pound.

You can also buy them directly if you don’t feel like picking them yourself, but the experience is quite fun. There are plenty of blueberries for everyone to pick, and the staff are friendly and helpful.

Recently, they also added raspberries, making the experience even tastier.

10. Go cross country skiing at Harris Farm

This huge dairy farm covers 500 acres and offers 40 kilometers of cross country ski trails. They are specially groomed for both classic and skate technique skiing and suit all levels of experience.

The place also includes a ski lodge with a nice lobby to enjoy hot drinks and snacks for when you need a break.

If this is your first time skiing, you can book lessons by appointment and rent all the needed equipment.

11. Indulge your sweet tooth at Thurston and Peters Sugarhouse

Many people described their ice cream from this venue as heavenly. It’s the maple syrup that makes all the difference, and you can purchase it separately at their shop.

They have a wide variety of syrups to choose from, including light, dark, and amber syrups with various grades.

This family-owned joint is run by friendly and helpful owners who will gladly help you find the right maple syrup for you.

They also offer tours of their property, explaining the entire creation process from start to finish. You will learn about the optimal conditions needed to create the perfect maple syrup.

12. Shop at Snell Family Farm

If you are looking for some fresh, organic fruits, vegetables, and other products, this is the best place to stop by. They also have unique herbs that you can’t find anywhere else, and plenty of beautiful flowers.

The sellers are friendly and knowledgeable; by shopping here, you will support the local economy and agriculture. When Halloween is approaching, you will also find plenty of pumpkins.

13. Have dinner at the Harris Turkey Farm

Here you will find some of the best gourmet pot pies and soups in the area, made with turkey that was raised right here at the farm.

The place is family run and their mantra is to raise the animals in the most humane way possible, giving them a better life which results in meat of a higher quality.

They also have a store with pottery and various gifts, wine, maple syrup and more.

14. Watch a show at the Saco River Theatre

The aim of this theatre is to enrich the local community by offering various plays, shows, programs, and exhibitions, to connect the locals with art and culture.

They work as a performing center of arts and a public forum; everyone is welcomed here. When first built in 1897, it was a chapel, before being used as the social center for Bar Mills. Later, it became an auction house before transforming into the theatre in 1990.

The owners and staff are very passionate and dedicated to art; you can see this in every show that you attend.

15. Stop by De Wolfe and Wood Rare Books

If you are passionate about reading and especially about old books, then this is the perfect place to stop by. They have a large collection of antique and rare books and publications of historical interest.

Don’t expect new and shiny books here; some of them are in really bad condition, but this is what makes them more interesting and authentic.

If you happen to own some old books and want to get rid of them, you can bring them here for an appraisal.