14 Best Things to Do in Westbrook (Maine)

Written by Veronique Raes
Updated on
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Westbrook is a city of around 17,000 people which is located in the Cumberland County of Maine. It was initially called Saccarappa, named after the waterfall with the same name found on the nearby river.

Part of the Falmouth city until 1814, it then became Stroudwater. Later on, the name was changed again to become Westbrook. This change was inspired by Colonel Thomas Westbrook, one of the first settlers – a mill operator but also a leader in Father Rale’s War.

In 1871, the town split into two parts, one of them eventually being added to Portland, while the other being officially incorporated as Westbrook in 1891.

When visiting Westbrook, take some time to check out the following things to do.

1. Admire life at Smiling Hill Farm

Smiling Hill FarmSource: Smiling Hill Farm / facebook
Smiling Hill Farm

If you have ever wondered how people live at a farm, how they raise animals, and how they do all the work, now is your chance to find out.

Here, you can take a leisurely stroll through the farm and view the goats, cows, sheep, donkeys, deer, ponies, and chickens.

There are playground tractors and climbing amusements for the kids, and at the end of the walk, you will receive an absolutely delicious homemade ice cream.

2. Stroll along the Westbrook River

Westbrook RiverSource: Maureen Milliken / shutterstock
Westbrook River

Spend a relaxing afternoon wandering the banks of the river admiring the beautiful views, including waterfalls, bridges, and boats in the harbor.

The river is gently flowing, the walking path is clean and well maintained, the buildings are small but modern, and the people are friendly.

This place has a nice mixture of natural scenery and manmade structures, so it’s definitely worth a visit.

3. Have a beer at the Mast Landing Brewing Company

Mast Landing Brewing CompanySource: Mast Landing Brewing Company / facebook
Mast Landing Brewing Company

You have probably worked up quite a thirst after your pleasant stroll along the river; what better way to quench your thirst than with a cold beer.

This local brewing company offers a wide variety of brews to choose from. The tasting room is large and they also have a gaming area.

You can watch sports games on the TV while you drink, but unfortunately, they don’t serve any food or snacks.

4. Catch a movie at Cinemagic

CinemagicSource: www.cinemagicmovies.com

If the weather doesn’t allow for hiking or sightseeing, or you simply want to relax while watching a good movie, then Cinemagic is the place to go.

The theatre is clean and well managed, with comfortable seats; it displays the latest Hollywood movies and the popcorn is mouthwatering. In order to avoid waiting in line, you can buy your tickets online.

5. Meander through Riverbank Park

Riverbank ParkSource: Kenneth C. Zirkel / Wikimedia
Riverbank Park

Yet another good place for some outdoor relaxation, this park has plenty of scenic trails to explore. It is suited for people of all ages, with some nice playgrounds for the kids.

There are always ducks to feed, and you can bring your dog along to join in the fun. Now and then, there are bands playing, so you can enjoy the views with some nice music.

Sit on a bench, have a picnic at the designated tables, or just walk around and enjoy nature.

6. Work out at Maine Warrior Gym

Maine Warrior GymSource: Maine Warrior Gym / facebook
Maine Warrior Gym

What often happens during a vacation is that you eat too much, indulge yourself with all kinds of treats, and end up gaining weight. While you should certainly have some fun and enjoy a few good meals, why not balance it out by enjoying a workout?

In Westbrook, you can do this at Maine Warrior Gym, where they organize various fitness classes for all ages and fitness levels.

They also have a Ninja Warrior obstacle course. If you’ve always wanted to give this a go, why not challenge yourself here.

7. Take the kids to Peekaboo Children’s Center

The young ones will love this place and have a lot of fun here. The center offers plenty of activities for various ages; it’s a safe, fun and educational center.

The venue is very clean; everyone that enters must take off their shoes. They have art activities, dolls, cars, bouncing objects and so much more.

The center can be rented for birthdays and other private parties for the kids.

8. Have Dinner at Jack’s Thai Cuisine

Jack’s Thai CuisineSource: Jack's Thai Cuisine / facebook
Jack’s Thai Cuisine

While not a traditional cuisine in the Maine area, the Thai food from this place is highly appreciated both by locals and tourists. They serve fresh and healthy recipes, made with high-quality local ingredients.

The dining area is simple yet cozy and the meals are delicious.

The restaurant is clean, the staff are friendly, and it doesn’t get too crowded. Overall, Jack’s Thai Cuisine is a great place to enjoy a family dinner and taste something new.

9. Have Dessert at Black Dinah Chocolatiers

Black Dinah ChocolatiersSource: Black Dinah Chocolatiers / facebook
Black Dinah Chocolatiers

After the Thai food you had at Jack’s Cuisine, it’s time for some award-winning, handcrafted chocolate truffles. You can find them at Black Dinah Chocolatiers, along with some Maine sea salt caramels and other goodies.

Their chocolate comes from reliable sources in Venezuela and Peru, while the other ingredients are fresh and produced in Maine. Besides tasting a truffle or two, you can also get some nicely packed gifts for friends or family.

After the visit here, you will definitely need to go and do another workout at Maine Warrior Gym.

10. Visit the Portland Museum of Art

Portland Museum Of ArtSource: Portland Museum of Art / facebook
Portland Museum Of Art

This is a great place for the entire family; some people consider it the best regional museum in the country. It displays various exhibits and collections, both from American and European culture.

Paintings, sculptures, handcrafts…you will find them all here. Plus, they offer free tours for schools, family activities, talks, movies and more.

This museum is so large that you can easily get lost in the art and spend a few hours here.

If you get tired, feel free to stop by their café, where they serve coffee, wine, beer, cider, and other goodies.

11. Wander along the Eastern Promenade

Eastern PromenadeSource: GraciePizzo / shutterstock
Eastern Promenade

Found in the nearby city of Portland, this is a great place to admire the ocean, the city, the harbor, and plenty of interesting buildings and monuments.

There are many benches and picnic tables along the way, as well as a playground for the kids and a dog park.

Take this walk at sunrise or sunset for even more impressive views; if you are lucky, you might see some beavers and other wild animals.

12. Climb the Portland Observatory

Portland ObservatorySource: travelview / shutterstock
Portland Observatory

If your thirst for viewing splendid ocean scenery is not satisfied by the Eastern Promenade, you can ascend this observatory to see everything from above.

This tower has been standing tall since the 1800s when it allowed locals to monitor the ships that were passing by.

Today, it is a popular tourist attraction and access is free. While climbing to the top, you can also admire the museum, which includes plenty of information about the history of the observatory and that of Portland itself.

13. Visit the Maine Narrow Gauge Railroad Company and Museum

Maine Narrow Gauge Railroad Company And MuseumSource: Maine Narrow Gauge Railroad Co. & Museum / facebook
Maine Narrow Gauge Railroad Company And Museum

After viewing so many boats and ships in the harbors of Portland, it’s time to see something different. This museum displays old trains and locomotives; you can even go for a ride in one.

Those who are passionate about trains will definitely love this museum, while the rest of the family will enjoy the train ride along Casco Bay; it will offer you a different perspective of Portland, as well as some splendid ocean views.

14. Enjoy more beer at the Shipyard Brewing Company

Shipyard Brewing CompanySource: facebook.com
Shipyard Brewing Company

Since you are already in Portland, why not try some of their locally brewed beer? This is one of the go-to places when it comes to good drinks, and it’s a family-owned business.

Over the years, they have produced more than 65 different types of beer, including some award-winning brews. All the varieties are listed on a big board; you take a piece of chalk and write the ones that you want on a custom serving tray.

You will receive all the beers on that tray, and taste them one by one. They also sell pizza and other snacks, so you can enjoy even more brews without overindulging.

14 Best Things to Do in Westbrook (Maine):

  • Admire life at Smiling Hill Farm
  • Stroll along the Westbrook River
  • Have a beer at the Mast Landing Brewing Company
  • Catch a movie at Cinemagic
  • Meander through Riverbank Park
  • Work out at Maine Warrior Gym
  • Take the kids to Peekaboo Children’s Center
  • Have Dinner at Jack’s Thai Cuisine
  • Have Dessert at Black Dinah Chocolatiers
  • Visit the Portland Museum of Art
  • Wander along the Eastern Promenade
  • Climb the Portland Observatory
  • Visit the Maine Narrow Gauge Railroad Company and Museum
  • Enjoy more beer at the Shipyard Brewing Company