Lakes and seasonal charm shape life in Oakland
The lake town of Oakland offers a peaceful Maine setting surrounded by water, woods and community ties. With two of the seven Belgrade Lakes—Messalonskee Lake and McGrath Pond—seeping into the town’s borders, Oakland has long been seen as a summer retreat, drawing boaters, kayakers and seasonal visitors to its rentable camps and waterfront properties. “Oakland is known for its beautiful natural surroundings,” says John Blouin, broker with LAER Realty Partners. “It’s part of the Belgrade Lakes region, and all seven lakes are within a short drive.” Settled in 1780 and shaped by its history as a mill town, Oakland’s downtown still reflects its past, with landmarks like Memorial Hall and a Carnegie library. Since then, the downtown area has added a community park and a handful of local eateries, maintaining a small-town vibe that’s especially popular with retirees. While the outdoorsy town isn’t bustling with action, next-door Waterville is. “Waterville is adjacent, home to Colby College and a vibrant downtown,” Blouin says.
Pleasant Point and Oakland Waterfront parks
Outdoor recreation centers around the town's lakes and wooded trails, offering a mix of water-based and land-based activities. On Oakland’s west side, Pleasant Point Park spans 75 acres along the banks of McGrath Pond, which connects to the larger Salmon Lake. In addition to lake access, the park provides miles of wooded trails. Closer to the town center, Oakland Waterfront Park sits at the northern edge of Messalonskee Lake and features a gazebo that hosts live music sessions in the summer, along with water access. “Many people have seasonal cottages on Messalonskee Lake,” Blouin says. “If you were to hop in your car, you can be at any of the seven lakes within 20 minutes.” Oakland is also home to several scenic hiking areas, including the Quarry Road Trails, which wind through forested terrain and offer year-round opportunities for outdoor exploration.
Lakefront cabins and farmhouses provide seclusion
Housing in Oakland reflects its small-town character and New England roots, with a median single-family sale price of around $385,000. More than 75% of homes are owner-occupied, and the architectural styles lean traditional; Cape Cods, Georgian Colonials, split-levels and farmhouses are common. Closer to the town center, homes sit on at least a quarter-acre, while the outskirts and lakeshore areas feature properties that are more spread out and often tucked into wooded lots or open fields. Prices range from about $190,000 for cabins around 1,000 square feet to over $900,000 for larger waterfront properties, though most homes fall somewhere between $250,000 and $350,000.
Messalonskee schools and Colby College serve students
Students can begin at Williams Elementary School, which receives a B-plus rating from Niche. Learners can then advance to Messalonskee Middle School, which holds a B. The B-minus-rated Messalonskee High School features an 826-seat Performing Arts Center that hosts the school’s programs and productions, as well as some of the community’s events and performances. For those looking to continue their education post-high school, Colby College is a private institution less than 3 miles east in Waterville.
The annual Oakfest brings community spirit
The community comes together late each summer to celebrate Oakfest. Held downtown behind the elementary school, festivities typically begin with a parade and a street dance. Attendees can also expect live music, food trucks, a street market and a Glow Ride, which involves the Messalonskee Trail Riders ATV Club decorating their ATVs with lights and glowing décor, followed by a ride through downtown Oakland.
Laid-back eats near more action in Waterville
Shopping and dining options in Oakland are modest but locally rooted, with a few small eateries and markets clustered around the town center. The Early Bird Restaurant is a go-to spot for classic American breakfasts, while Oakland House of Pizza offers a laid-back counter-serve experience with pizza and sandwiches. Buddies Groceries serves as the neighborhood market, stocking produce and everyday essentials. For more variety, residents often head east to Waterville, a larger neighboring city with a broader selection of stores and restaurants. In addition to Walmart and Hannaford, there’s a movie theater, an art museum, and a stretch of Main Street lined with popular restaurants. MaineGeneral Hospital is also located in Waterville.
Back roads link the lakes, and Interstate 95 is nearby
While there are no public buses or trains, residents here can get around town on a network of two-lane country roads that weave through the community and connect them to the surrounding lakes. “The town’s main road follows along Messalonskee Lake, which is a scenic ride,” says Blouin. Interstate 95 runs along the east side of Oakland, offering a direct route to Augusta, about 19 miles south. For further trips, Portland International Jetport is around 75 miles south.
Written By
Mary Beth Greene
