Nestled along the Presumpscot River, Westbrook, Maine, is far more than just a charming suburb of Portland; itโs a vibrant destination brimming with its own unique character, natural beauty, and a burgeoning culinary and craft scene. Forget the notion that you need to be in the bustling heart of a major city to experience true New England charm. Westbrook offers that quintessential blend of small-town warmth and modern amenities, making it an ideal getaway for families, solo adventurers, and couples alike.
Youโll discover a community that prides itself on its scenic riverfront, local businesses, and easy access to some of Maineโs most iconic attractions. The best time to visit is undoubtedly late spring through early fall, when the weather is perfect for outdoor explorations and the local establishments are in full swing. Pack comfortable shoes, an adventurous spirit, and get ready to uncover the delightful surprises awaiting you in Westbrook.
Admire life at Smiling Hill Farm

Prepare to step into a slice of idyllic farm life at Smiling Hill Farm, a true gem that has been a working dairy farm for over 200 years. This isn’t just a place to observe; it’s an immersive experience where you can connect with nature and agriculture. You will find yourself enchanted by the friendly farm animals, from curious goats and playful calves to clucking chickens and majestic horses.
Beyond the petting zoo, you can witness the daily operations of a dairy farm, learning about where your milk comes from. What truly sets Smiling Hill Farm apart is its commitment to education and family fun, offering hayrides, a delicious ice cream stand with flavors made from their own dairy, and even a small museum showcasing the farm’s rich history. Itโs a nostalgic journey back to simpler times, perfect for creating lasting memories with loved ones.
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Stroll along the Westbrook River

One of Westbrookโs most defining features is the Presumpscot River, and a stroll along the Westbrook River is an absolute must-do. This tranquil waterway meanders through the heart of the city, offering a serene escape and beautiful natural scenery right in an urban setting. You can wander along well-maintained paths that hug the riverbanks, providing picturesque views and opportunities for peaceful reflection.
What makes this experience unique is the blend of natural beauty with glimpses of Westbrookโs industrial past and present. You might spot local wildlife, from ducks gliding gracefully on the water to various bird species flitting among the trees. Itโs an ideal activity for those seeking a gentle walk, a refreshing jog, or simply a quiet moment to enjoy the outdoors. The river truly is the lifeblood of Westbrook, connecting its parks and community spaces.
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Have a beer at the Mast Landing Brewing Company

For craft beer enthusiasts, a visit to Mast Landing Brewing Company is an essential stop on your Westbrook itinerary. This brewery has quickly become a local favorite, renowned for its innovative brews and welcoming taproom atmosphere. What sets Mast Landing apart is their dedication to crafting a diverse range of beers, from crisp IPAs and robust stouts to experimental sours and refreshing lagers, ensuring thereโs something to please every palate.
You can enjoy a flight of tasters to discover your new favorite, or settle in with a full pint and soak in the vibrant, friendly ambiance. The taproom often hosts food trucks and live music, making it a lively hub for both locals and visitors. Itโs a fantastic place to unwind after a day of exploring, meet new people, and savor the taste of Maineโs thriving craft beer scene.
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Catch a movie at Cinemagic

While the specific Cinemagic location in Westbrook may have changed, the experience of catching a movie remains a timeless pleasure, and the area still offers opportunities for this classic pastime. This entry celebrates the joy of the big screen, the aroma of popcorn, and the shared excitement of a cinematic journey.
You can immerse yourself in the latest blockbusters or discover an independent film, all from the comfort of a darkened theater. What makes a movie outing special is its universal appeal, providing an easy and enjoyable way to relax and escape for a few hours, whether youโre on a date, with family, or simply seeking some solo entertainment. Itโs a perfect option for a rainy day, a casual evening, or when you simply want to kick back and let a story unfold before your eyes.
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Meander through Riverbank Park

Riverbank Park is a verdant oasis nestled along the Presumpscot River, offering Westbrook residents and visitors a beautiful space to relax, play, and connect with nature. When you meander through this park, youโll discover well-maintained walking trails that provide stunning views of the river and its surroundings.
What makes Riverbank Park particularly special is its thoughtful design, featuring a playground for children, open green spaces perfect for picnics or throwing a frisbee, and even a boat launch for those who wish to explore the river by kayak or canoe. Itโs a versatile spot that caters to a wide range of interests, from families looking for outdoor fun to individuals seeking a peaceful retreat. The park frequently hosts community events and concerts, adding to its vibrant atmosphere and making it a true hub of Westbrook life.
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Work out at Maine Warrior Gym

For those who love an active challenge or are curious about a unique fitness experience, working out at Maine Warrior Gym is an exhilarating opportunity. This isn’t your average gym; itโs a dedicated facility inspired by the popular American Ninja Warrior television show, featuring a variety of obstacles designed to test your strength, agility, and problem-solving skills.
You can swing across monkey bars, scale warped walls, balance on precarious beams, and tackle challenging climbing structures. What makes Maine Warrior Gym truly special is its welcoming environment for all skill levels, from beginners looking for a fun new way to exercise to seasoned athletes honing their ninja skills. It’s an incredibly engaging way to get a full-body workout, build confidence, and unleash your inner warrior in a safe and supportive setting.
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Take the kids to Peekaboo Childrenโs Center

Families traveling with young children will find a delightful haven at Peekaboo Childrenโs Center, a vibrant and engaging indoor play space designed specifically for little ones. This center offers a safe, stimulating, and imaginative environment where kids can explore, create, and burn off energy, regardless of the weather outside. You will discover a variety of play zones, from soft play areas for toddlers to interactive exhibits that encourage imaginative role-playing, building, and problem-solving.
What makes Peekaboo Childrenโs Center unique is its focus on child-led play and its clean, well-maintained facilities. Itโs the perfect spot for parents to relax while their children are entertained and engaged in meaningful play. It provides a much-needed break for families on the go, ensuring that even the youngest travelers have a memorable and fun experience in Westbrook.
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Have Dinner at Jackโs Thai Cuisine

Embark on a culinary journey to Thailand without leaving Westbrook by having dinner at Jackโs Thai Cuisine. This highly-regarded restaurant is a local favorite, celebrated for its authentic flavors, fresh ingredients, and warm, inviting atmosphere. You can savor a wide array of traditional Thai dishes, from fragrant curries and savory noodle plates like Pad Thai to spicy stir-fries and refreshing salads.
What makes Jackโs Thai Cuisine stand out is its consistent quality and the ability to customize dishes to your preferred spice level, ensuring a perfect meal whether you like it mild or fiery hot. Itโs a wonderful spot for a cozy dinner with family or friends, offering a taste of international cuisine right in the heart of Westbrookโs dining scene. Prepare your taste buds for an explosion of delicious, aromatic flavors.
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Have Dessert at Black Dinah Chocolatiers

Indulge your sweet tooth and experience artisanal chocolate at its finest by having dessert at Black Dinah Chocolatiers. While their primary production is on an island, their Westbrook location brings their exquisite creations closer to you. This is not just a place to buy chocolate; itโs an experience in gourmet confectionery.
You will discover an array of beautifully crafted truffles, bars, and other confections, each made with high-quality ingredients and incredible attention to detail. What makes Black Dinah Chocolatiers truly special is their commitment to unique flavor combinations, often incorporating local Maine ingredients and unexpected pairings that delight the palate. Itโs the perfect place to pick up a luxurious treat for yourself, find a sophisticated gift, or simply enjoy a moment of pure, unadulterated chocolate bliss. Their creations are as much works of art as they are delicious desserts.
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Visit the Portland Museum of Art

While technically located in nearby Portland, a visit to the Portland Museum of Art is an absolute must-do and easily accessible from Westbrook, making it a perfect cultural excursion. This prestigious museum houses an impressive collection spanning European, American, and contemporary art, with a particular strength in works by Maine artists and those inspired by the state’s rugged beauty.
You will wander through diverse galleries, encountering masterpieces by renowned artists alongside thought-provoking contemporary installations. What makes the Portland Museum of Art unique is its intimate scale, allowing for a deeply engaging experience without feeling overwhelming, and its commitment to showcasing the rich artistic heritage of the region. Itโs a fantastic opportunity to immerse yourself in art and culture, offering a tranquil yet stimulating escape that complements Westbrookโs local charm.
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Wander along the Eastern Promenade

For breathtaking coastal views and invigorating fresh air, wander along the Eastern Promenade in Portland, another easily accessible and highly recommended extension of your Westbrook adventure. This iconic public park stretches for miles along the waterfront, offering panoramic vistas of Casco Bay, its islands, and the distant coastline.
You can stroll or jog along the paved path, find a bench to simply gaze at the sailboats, or enjoy a picnic on the expansive grassy slopes. What makes the Eastern Prom truly special is its blend of natural beauty with historical significance, featuring landmarks like the Portland Observatory and remnants of Civil War-era fortifications. Itโs a beloved spot for locals and visitors alike, perfect for an active outing, a romantic sunset view, or simply soaking in the quintessential Maine coastal ambiance.
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Climb the Portland Observatory

Standing proudly atop Munjoy Hill in Portland, the Portland Observatory offers a unique historical experience and unparalleled views that are well worth the short drive from Westbrook. This historic maritime signal tower, built in 1807, is the only remaining wooden signal tower of its kind in the United States.
You can climb the narrow, winding stairs to the top, where a knowledgeable guide will share fascinating stories of Portlandโs maritime past and the tower’s crucial role in communicating with incoming ships. What makes the Portland Observatory truly special is not just its historical significance, but the incredible 360-degree views it provides of the city, Casco Bay, and the surrounding islands. It’s an essential stop for history buffs, photographers, and anyone looking for a unique perspective on Portland’s working waterfront.
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Visit the Maine Narrow Gauge Railroad Company and Museum

Step back in time and experience the charm of historic rail travel at the Maine Narrow Gauge Railroad Company and Museum, conveniently located in Portland and easily reachable from Westbrook. This unique attraction offers a delightful journey along Casco Bay aboard antique narrow-gauge trains, providing passengers with picturesque views and a glimpse into Maineโs rich railroad heritage.
You will ride in beautifully restored passenger cars, pulled by vintage locomotives, along a scenic route that hugs the coastline. What makes this museum and railroad truly special is its dedication to preserving and sharing the story of Maineโs narrow-gauge railways, which once played a vital role in the state’s logging and industrial history. Itโs an engaging and educational experience for all ages, particularly captivating for families and history enthusiasts.
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Enjoy more beer at the Shipyard Brewing Company

No trip to Maineโs beer scene is complete without enjoying more beer at the Shipyard Brewing Company, a true pioneer in the New England craft beer movement, located in Portland and an easy drive from Westbrook. Shipyard has been brewing award-winning beers for decades, establishing itself as a cornerstone of Maine’s thriving craft beverage industry.
You can take a brewery tour to learn about their brewing process, from grain to glass, and then settle into their tasting room or pub to sample a wide array of their classic and seasonal brews. What makes Shipyard special is its long-standing history, its commitment to quality, and its diverse portfolio of beers, from their popular summer ale to their robust pumpkinhead. Itโs a fantastic opportunity to deepen your appreciation for craft beer and experience one of Maineโs most iconic breweries.
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Plan Your Visit
Westbrook, Maine, truly is a destination that defies expectations, offering a delightful blend of local charm, natural beauty, and exciting attractions. From the pastoral simplicity of Smiling Hill Farm to the urban buzz of its riverside parks and innovative breweries, you will discover a community that warmly welcomes you. Its strategic location also makes it the perfect launching pad for exploring the iconic coastal gems of nearby Portland, seamlessly connecting you to world-class art, historic landmarks, and stunning ocean vistas.
Don’t just pass through; immerse yourself in Westbrook’s unique character and let its vibrant spirit captivate you. With this guide in hand, you’re ready to plan an unforgettable adventure filled with diverse experiences, delicious food, and lasting memories. Start envisioning your Maine getaway today โ Westbrook awaits!
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