15 Best Things to Do in Freeport (Maine)

Freeport, located in Cumberland County, Maine, has gained fame for its outlet stores, but there is so much more to this charming town that attracts visitors like myself. The history of Freeport dates back to the late 17th century when settlers first arrived in the area. Initially part of North Yarmouth, Freeport gained its independence in 1789 after meeting the requirements of having a church, minister, and congregation.

In the early days, the livelihood of the locals revolved around shipbuilding and fishing. Today, you can still find traces of this maritime heritage in the marina and yacht club, which occupy the same spaces where these activities once thrived. Additionally, Freeport was known as a farming town, and the canning industry played a significant role in its economy.

While the town’s landscape has evolved over the years, with the disappearance of many wooden buildings, remnants of Freeport’s rich history can still be discovered. Exploring the history of Freeport is a fascinating journey, and there are plenty of opportunities to delve into it as part of the 15 Best Things to do in Freeport.

1. Freeport Historical Society

With great interest in history, I was thrilled to learn about the Freeport Historical Society and its remarkable contributions to preserving the town’s rich heritage. Celebrating its 50th year in 2019, the society has played a pivotal role in documenting and protecting the valuable historic buildings and districts that make Freeport so special.

At the heart of the society’s operations lies the iconic Harrington House, a true gem in itself. Constructed in 1830 by a prominent merchant bearing the same name, this magnificent structure originally sat on a sprawling 14-acre parcel of land. Over the years, the house changed hands multiple times, until it eventually found its purpose as the headquarters of the Freeport Historical Society.

Inside the walls of Harrington House, dedicated individuals have worked tirelessly to create a comprehensive record of Freeport’s captivating history. Through meticulous research, they have assembled an impressive inventory of historic buildings and districts, ensuring that these treasures are preserved for future generations to appreciate.

The Freeport Historical Society’s unwavering dedication to its mission has not only enriched our understanding of the town’s heritage but also fostered a deep sense of pride among the community. By celebrating and preserving Freeport’s history, the society has created a lasting legacy that serves as a reminder of the town’s unique identity.

2. Pettengill Farm

Exploring the enchanting Pettengill Farm, a 19th-century saltwater farm nestled on the scenic Harraseeket estuary, was a memorable experience. Owned by the Historical Society and spanning an impressive 140 acres, this captivating farm offers a diverse landscape that transitions seamlessly from salt marshes to lush orchards, expansive fields, and enchanting woodlands.

Stepping foot onto the farm, I couldn’t help but marvel at its well-preserved authenticity. It was fascinating to learn that even though Mildred Pettengill resided here until 1970, just five years before generously donating the property to the Historical Society, the farm had never been equipped with modern conveniences such as plumbing or central heating. This lack of modernization only added to the farm’s charm, providing a glimpse into a simpler way of life that once thrived in this picturesque corner of Maine.

As I wandered through the farm’s grounds, I found myself captivated by the incredible variety of flora that adorned the landscape. Fragrant lilacs and roses painted the air with their sweet scents, while vibrant hollyhocks and dahlias added splashes of color to the surroundings. It was a visual feast for the senses, a testament to the love and care that the Historical Society has poured into maintaining the farm’s natural beauty.

Inside the farm’s buildings, a hidden treasure awaited in the form of intriguing etchings depicting majestic ships and marine life. These artistic pieces provided a glimpse into the maritime heritage that shaped the region and added another layer of historical depth to the Pettengill Farm experience.

The Pettengill Farm stands as a testament to a bygone era, inviting visitors like me to step back in time and connect with the land, the sea, and the stories of those who once called this place home.

3. Casco Castle

The quaint South Freeport Village holds a hidden gem from the past—the magnificent tower of Casco Castle. With both land and sea access, South Freeport was once a bustling hub of transportation, with the railroad and steamboat being the preferred modes of travel in the 19th century. Locals traversed the village’s charming streets in horse-drawn carriages or sleighs, creating a nostalgic ambiance that still lingers today.

Perched proudly on a prominent spot, overlooking the glistening bay, stands the awe-inspiring tower—a testament to the craftsmanship and vision of a local man named Benjamin Franklin Dunning. Rising an impressive 100 feet into the sky, this architectural marvel stands as a lasting reminder of South Freeport’s storied past. As I gazed up at the tower, I marveled at the dedication and effort it must have taken to transport the stones up the steep hill to construct this towering structure. The panoramic views that awaited atop the tower were nothing short of breathtaking, offering a captivating vista of the bay that stretched out before me.

Standing in the presence of Casco Castle’s tower, I couldn’t help but feel a profound sense of connection to the village’s history and the hardworking individuals who once called this place home. The tower’s enduring presence serves as a testament to their perseverance and the indomitable spirit that shaped South Freeport.

The tranquil waters shimmered in harmony with the gentle breeze, while the tower stood tall and proud, a silent witness to the passage of time. It was a scene of serenity and natural grandeur that spoke volumes about the allure of South Freeport.

4. Winslow Park

As I delved more into Winslow Park, I couldn’t help but feel a sense of reverence for the Winslow Family, the early settlers who left their mark on Maine’s history in the early 18th century. This picturesque park, bearing their name, proved to be a haven of outdoor activities both on land and at sea.

Exploring the park’s numerous trails, I was in awe of the breathtaking viewpoints that revealed the stunning beauty of the bay, harbor, and the remarkable Casco Castle. Each step I took immersed me deeper into the natural wonders that Winslow Park had to offer.

The park’s expansive camping area beckoned to families seeking an overnight escape in the heart of nature. With the option to book a campsite, we could indulge in the joy of spending quality time under the starry night sky. The park’s pristine beach enticed me to dip my toes in the refreshing waters, while the allure of kayaking offered a thrilling adventure amidst the gentle waves.

Winslow Park also provided the perfect backdrop for special occasions. The opportunity to book the park for a memorable gathering added an extra touch of magic to any celebration. And during the vibrant summer months, the park came alive with the melodies of regular concerts, filling the air with enchanting music that harmonized with the natural surroundings.

From the breathtaking trails and captivating viewpoints to the camping adventures and beachside bliss, this park truly had it all. The Winslow Family’s legacy was alive and well in this remarkable haven of nature.

5. Wolfe’s Neck Woods State Park & Center

Wolfe’s Neck Woods State Park & Center, a generous donation to Freeport 50 years ago, I marveled at the vastness of its 200-acre parcel of land. Nestled between the picturesque Casco Bay and the tranquil Harraseeket River, this peninsula was a hidden gem just minutes away from the bustling heart of Freeport.

Towering pines and majestic hemlocks stretched as far as the eye could see, providing a serene canopy that offered respite from the outside world. As I explored deeper into the park, I discovered the captivating juxtaposition of the salt marsh estuary and the rugged shoreline. The harmonious blend of these natural elements created a tapestry of landscapes that constantly captivated my senses.

Immersed in the tranquility of the woods, I embarked on nature walks that led me deeper into the heart of this enchanting sanctuary. As I meandered along the well-maintained paths, I couldn’t help but feel a sense of awe at the beauty that surrounded me. I kept my eyes peeled for the elusive ospreys, who called nearby Goggin Island home during the summer months before embarking on their journey to South America. Spotting these magnificent birds of prey soaring through the sky was a sight to behold, a testament to the harmonious relationship between wildlife and nature in this protected haven.

Wolfe’s Neck Woods State Park & Center offered a perfect escape from the hustle and bustle of everyday life, allowing me to reconnect with the wonders of the natural world. The peaceful melodies of chirping birds and the gentle rustle of leaves beneath my feet created a symphony of tranquility that echoed through the forest. With every step, I felt a deep sense of gratitude for the individuals who had donated this precious land, ensuring its preservation for future generations to enjoy.

6. Bradbury Mountain State Park

When I went to Bradbury Mountain State Park, I was filled with anticipation for the breathtaking views that awaited me. Despite its modest height of just under 500 feet, the summit promised magnificent vistas of the expansive Casco Bay, particularly during the vibrant fall season when the colors of the foliage painted a picturesque scene.

With over 20 miles of trails winding through the park, I had ample opportunities to immerse myself in nature’s embrace. Hikers, bikers, and even horse riders reveled in the diverse pathways that catered to various outdoor enthusiasts. As I ventured along the well-maintained trails, I marveled at the surrounding beauty and tranquility, feeling a sense of connection with the natural world around me.

Bradbury Mountain State Park was not just a haven for outdoor adventurers; it was also a sanctuary for families seeking quality time together. The park offered camping facilities that provided a perfect opportunity to spend a night under the stars, sharing stories and creating lasting memories. Children frolicked in the playground, their laughter filling the air with joy and excitement.

Remnants of the past stood as gentle reminders of the area’s heritage, adding a touch of intrigue and fascination to my journey. Among the park’s treasures, I discovered a diverse array of flora, including the elusive and rare orchid. Despite the temptation to pluck a delicate blossom, I respected nature’s delicate balance and left the flower undisturbed, appreciating its beauty in its natural habitat.

Bradbury Mountain State Park was a sanctuary where nature’s wonders unfolded, offering a respite from the chaos of everyday life. The serene trails, captivating views, and vibrant flora created a harmonious symphony that echoed through the park.

7. Desert of Maine

The Desert of Maine is an expansive 40-acre area, adorned with a unique blend of glacial silt and flourishing vegetation, presented a sight unlike anything I had ever witnessed. However, it was important to note that despite its name, the Desert of Maine was not a true desert and received abundant rainfall, which contributed to its distinctive charm.

Eager to delve deeper into this intriguing landscape, I decided to go on a guided tour offered at the site. With an experienced guide leading the way, I was immersed in the fascinating history and geological wonders of the area. As we ventured through the Desert of Maine, I gained a newfound appreciation for its formation and the forces of nature that shaped its distinct features.

Adjacent to the desert, I discovered a delightful barn museum that showcased artifacts and memorabilia, providing further insight into the rich heritage of the region. It was a treasure trove of knowledge, offering a glimpse into the past and allowing visitors like myself to connect with the captivating stories embedded within this remarkable landscape.

For young adventurers seeking an extra thrill, the Desert of Maine offered an exciting gemstone hunting experience. Kids had the opportunity to embark on their own treasure hunt, searching for precious gemstones for an additional fee. It was a delightful activity that added a touch of excitement to the visit and provided a memorable keepsake for those lucky enough to find a hidden gem.

For those looking to extend their stay, the Desert of Maine provided convenient camping facilities. It was a perfect opportunity to immerse oneself in the serene surroundings and spend the night under the starry sky, surrounded by the allure of the desert. Additionally, early May until winter brought the opportunity to partake in a lively game of disc golf. Campers were given priority in the mornings, allowing them to enjoy this engaging sport and create cherished memories amidst the breathtaking landscape.

8. L.L. Bean Flagship Store

In 1912, Leon Leonwood Bean, a passionate hunter and fisherman, opened the doors of a modest one-room store in Freeport. The LL Bean Flagship Store is a small shop that became the birthplace of a legacy that would transcend generations. Initially specializing in hunting boots, Bean’s dedication to quality and his understanding of the needs of outdoor enthusiasts quickly earned him a loyal following.

Over the years, it was Bean’s grandson who propelled the family business to new heights, expanding its offerings and cementing its reputation as a leading retailer in outdoor clothing, footwear, and camping gear. Today, LL Bean remains family-owned, a testament to the enduring values and commitment to excellence that have shaped its success.

One of the remarkable aspects of the LL Bean Flagship Store in Freeport is its unwavering dedication to serving its customers. With only a few exceptions for special occasions, the store proudly opens its doors around the clock, 24 hours a day, 7 days a week. This commitment ensures that visitors like myself can indulge in the joy of shopping at any time that suits our convenience, embracing the freedom to explore the vast array of high-quality merchandise and experience exceptional customer service.

The store showcased a diverse range of products designed to withstand the rigors of nature while providing optimal comfort and performance. Whether one sought hiking boots, rugged camping equipment, or stylish outdoor clothing, LL Bean offered an impressive variety to fulfill every outdoor enthusiast’s desires.

9. Leon Gorman Park

Freeport has always been a delightful destination for indulging in some much-needed retail therapy. However, amidst the hustle and bustle of the town, I discovered a tranquil haven that offered a serene escape from the shopping frenzy—the Leon Gorman Park. Located conveniently close to the center of Freeport, this charming park holds a special significance as it was graciously donated to the town by none other than LL Bean, the iconic retailer, and is named after the grandson of its founder.

Spanning across eight acres, it may not be the largest park, but it certainly offers a delightful retreat for locals and visitors alike. The highlight of the park is the inviting picnic pavilion, where one can enjoy a leisurely lunch break from the day’s activities.

It was a pleasant stroll that allowed me to immerse myself in the tranquility of nature. The well-maintained trail led me through a variety of scenic landscapes, offering glimpses of vibrant flora and fauna along the way. The park’s lush grassy area provided an inviting spot for lounging or engaging in outdoor activities, such as playing frisbee or tossing a ball with friends and family.

One feature that particularly caught my attention was the small ice-skating area nestled within the park. Although it may be modest in size, it exuded a nostalgic charm that evoked memories of winter fun. I imagined the joyous laughter of children and the graceful gliding of skaters during the colder months, adding an extra touch of magic to the park’s serene ambiance.

10. Maine Audubon – Mast Landing Sanctuary

At the heart of every Audubon site lies a commitment to creating a haven for wildlife, and the Maine Audubon – Mast Landing Sanctuary on the Harraseeket Estuary is no exception. As I stepped foot onto the sanctuary, I instantly felt a connection with nature and the underlying mission to preserve and protect the diverse ecosystem.

The sanctuary boasts a variety of enchanting landscapes, each offering a unique glimpse into the wonders of the natural world. Meandering through the trails, I found myself immersed in a tapestry of sights and sounds that unfolded around me. A gentle stream meandered through the sanctuary, its tranquil waters glistening in the sunlight. Nearby, a vast salt marsh teemed with life, providing a vital habitat for a myriad of fascinating creatures.

These towering guardians of the sanctuary added a sense of tranquility, casting dappled shadows upon the forest floor. Beyond the woodlands, open fields and orchards stretched out, inviting visitors to embrace the beauty of the natural landscape.

While exploring the sanctuary in the warmer months, I encountered fellow hikers who were drawn to its serene beauty. The trails provided the perfect opportunity to immerse myself in the natural splendor, with each step revealing new discoveries and hidden treasures. But the sanctuary’s allure didn’t diminish in the winter; instead, it transformed into a picturesque wonderland where cross-country skiers delighted in gliding through the snow-covered trails, surrounded by a serene winter landscape.

11. Porterfield Cider

In recent years, I had the pleasure of discovering a hidden gem known as Porterfield Cider. This charming establishment breathed new life into an old farm dating back to 1890, transforming it into a thriving cider production center. Nestled within 117 acres of enchanting fields, picturesque gardens, winding woodland trails, and flourishing orchards, Porterfield Cider has become a destination that beckons visitors from far and wide.

The farm’s fields and gardens were teeming with vibrant, locally grown produce that changed with the seasons, offering a delightful feast for the senses. From juicy berries in the summertime to crisp apples in the fall, the farm’s bounty embraced the true essence of farm-to-table goodness.

However, it was the cider that stole the spotlight and captured the imagination of all who visited. Made with meticulous care and dedication, the cider at Porterfield Cider showcased the artistry of traditional cider production. The aroma of freshly pressed apples filled the air, while the distinct flavors danced on my palate with each sip. I found myself drawn to the inviting seating areas, where I could indulge in a glass of their exquisite cider while savoring the accompanying local delights, such as artisanal cheeses and crusty bread.

For those seeking a truly immersive experience, Porterfield Cider offered the opportunity to rent the beautifully renovated farmhouse. The farmhouse, once plagued by years of decay, had been lovingly restored, breathing new life into its timeworn walls. I could only imagine the joy of waking up to the serene countryside vistas and savoring the tranquility of this picturesque setting.

12. Cruising the Bay

If you find yourself in Freeport, I highly recommend embarking on an unforgettable cruise that ventures out into the vast Atlantic Ocean. While there may be certain times of the year when this isn’t practical, on a beautiful day, it’s an opportunity that should not be missed.

Freeport offers a range of captivating tours, each offering its own unique experience. If you’re seeking an exhilarating adventure, consider indulging in a deep-sea fishing excursion. While there are no guarantees when it comes to reeling in a catch, the thrill of the chase and the camaraderie of fellow fishing enthusiasts make for an enjoyable and memorable outing.

As you set sail from Freeport Bay, you’ll be treated to awe-inspiring views of the picturesque coastline. The scenery takes on a whole new dimension when observed from the gentle rocking of a boat on the sparkling sea. You might even choose to embark on a lobstering tour, where you’ll witness firsthand the traditional techniques used to harvest these delectable crustaceans. Alternatively, venture out in search of Atlantic Seals, observing these majestic creatures in their natural habitat.

For a truly enchanting experience, consider visiting Eagle Island State Park during your cruise. This idyllic island, known for its captivating beauty, served as the summer home of Admiral Robert Peary, the renowned Arctic explorer.

13. Hedgehog Mountain Trail

I want to share with you a hidden gem in Freeport: the Hedgehog Mountain Trail. This little-known trail spans across 196 acres of stunning natural beauty and is the perfect destination for a fun-filled family day out. Whether you visit during the summer or winter, there’s something for everyone to enjoy.

The Hedgehog Mountain Trail remains open year-round, offering different experiences depending on the season. When winter blankets the landscape with snow, it transforms into a winter wonderland, perfect for snowshoeing or skiing adventures. The crisp air and glistening trails create a magical atmosphere that is sure to delight both young and old. During the rest of the year, the trail is ideal for hiking or biking, allowing you to immerse yourself in the breathtaking scenery at your own pace.

As you traverse the Hedgehog Mountain Trail, you’ll have the opportunity to explore a diverse landscape. The trail winds its way through picturesque pine and hemlock forests, providing shade and serenity along the way. You’ll also encounter remnants of history as you navigate over and around old stone walls, a testament to the area’s rich past.

One of the best things about the Hedgehog Mountain Trail is that you can bring your furry friends along for the adventure. As long as they are kept on a leash, your beloved dogs can join in on the fun and explore the wonders of nature with you.

Convenient parking is available adjacent to the trail, making it easily accessible for all. While the Hedgehog Mountain Trail may currently be a well-kept secret, I have a feeling that won’t last for long. Its scenic beauty, well-maintained trails, and family-friendly atmosphere make it an unforgettable destination that is bound to capture the hearts of many outdoor enthusiasts.

14. Maine Beer Company

If you’re a craft beer enthusiast, then a visit to the Maine Beer Company is an absolute must when you’re in the state of Maine. This renowned brewery embraces the spirit of Maine’s craft beer culture and warmly welcomes visitors who are eager to explore their impressive selection of brews.

As soon as you step foot inside the Maine Beer Company, you’ll sense the passion and dedication that goes into their craft. With each sip, you’ll be treated to a unique and distinct flavor experience. From their refreshing IPAs to their smooth lagers, flavorful pale ales, and rich stouts, there’s something to satisfy every beer lover’s palate.

The success of the Maine Beer Company has been remarkable, and it’s no surprise that they’re planning to expand their operations. This exciting news means that even more beer enthusiasts will have the opportunity to enjoy their exceptional brews and immerse themselves in the vibrant beer culture that Maine has to offer.

While the main attraction is, of course, the incredible selection of beers, the Maine Beer Company also caters to your snacking needs.

15. Coastal Highway US 1

Driving along US 1, I couldn’t help but feel a sense of wonder as I passed by quaint villages and their beautifully preserved historic houses. Each village had its own unique character and story to tell, with their charming architecture and well-preserved landmarks. It felt like stepping back in time, immersing myself in the rich heritage of the region.

But it was the stunning coastal vistas that truly stole the show. The sight of the sparkling ocean stretching out as far as the eye could see was simply mesmerizing. The Coastal Highway offers glimpses of secluded coves, rocky cliffs, and sandy beaches, creating a truly unforgettable backdrop for my journey.

While I understand that spending excessive time in the car might not be everyone’s cup of tea, I assure you that driving along a stretch of US 1 is well worth it. The ever-changing scenery and the allure of hidden gems along the way make for an enriching and rewarding experience.