Imagine a place where the scent of pine needles mingles with the aroma of freshly baked goods, where crystal-clear lakes invite you to paddle, and where a vibrant arts scene thrives amidst charming New England landscapes. Welcome to Oakland, Maine! Nestled in the heart of the Kennebec Valley, Oakland offers a delightful blend of outdoor adventure, rich history, and surprising cultural gems. It’s a destination that often flies under the radar, making it perfect for those seeking authentic experiences away from the bustling tourist crowds.
Whether you’re a nature lover, a history buff, a foodie, or an art enthusiast, you’ll find something truly special here. The best time to visit Oakland is from late spring through early fall, when the weather is glorious and all attractions are in full swing, though winter offers its own snowy charm. Prepare to be enchanted as we uncover the 15 best things to do in this hidden Maine treasure, promising memories you’ll cherish long after you leave.
Riverside Farm Market and Café
Your journey into Oakland’s local flavor must begin at Riverside Farm Market and Café, a true cornerstone of the community and much more than just a place to grab a bite. This isn’t just a market; it’s an experience, embodying the farm-to-table ethos with a warm, welcoming Maine spirit. You’ll discover a bounty of fresh, locally sourced produce, artisanal cheeses, homemade baked goods, and unique Maine-made products perfect for souvenirs or a delicious picnic. The café itself serves up hearty breakfasts and lunches, featuring ingredients straight from the farm or neighboring producers.
Imagine sipping a hot coffee while enjoying a freshly baked scone, or savoring a sandwich crafted with garden-fresh vegetables. It’s a place where locals gather, sharing stories and laughter, and where visitors instantly feel at home. The atmosphere is authentically rustic and inviting, making it ideal for families seeking wholesome food, couples looking for a cozy breakfast spot, or solo travelers wanting to soak in the local vibe. Don’t miss their seasonal specials, which often highlight the freshest produce of the moment.
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Snow Pond Cruises
For an entirely different perspective of Oakland’s natural beauty, you absolutely must embark on one of the Snow Pond Cruises. Great Pond, one of Maine’s largest and most picturesque lakes, is the star here, and a cruise offers an unparalleled way to appreciate its sprawling beauty, dotted with islands and framed by lush forests. You’ll glide across the serene waters, feeling the gentle breeze and soaking in the tranquil ambiance.
Whether you choose a scenic daytime tour, a romantic sunset cruise, or a specialized nature excursion, each journey provides unique insights into the lake’s ecosystem and the surrounding landscape. Keep an eye out for loons, eagles, and other local wildlife that call Great Pond home. The cruises often feature knowledgeable guides who share fascinating facts about the area’s history, geology, and local lore, making it an educational as well as relaxing experience. This activity is perfect for all ages, offering a peaceful escape for couples, a fun adventure for families, and a serene outing for solo travelers seeking natural beauty.
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Tree Spirits Winery and Distillery
Step into the enchanting world of Tree Spirits Winery and Distillery, a unique establishment that truly captures the essence of Maine’s innovative spirit. What makes Tree Spirits stand out is their dedication to crafting wines and spirits from local fruits, particularly apples, pears, and even blueberries, rather than traditional grapes. You’ll be fascinated by the distinct flavors and aromas derived from these Maine-grown ingredients, offering a refreshingly different tasting experience. Imagine sampling a crisp apple wine, a smooth pear brandy, or a robust maple liqueur, each sip telling a story of the region’s agricultural bounty.
A visit typically includes a tour of their modest but efficient facility, where you can learn about their unique fermentation and distillation processes, followed by a guided tasting. The passion of the owners is palpable, making the experience both informative and incredibly enjoyable. This destination is ideal for adult groups, couples, and solo travelers interested in local craft beverages and unique culinary experiences. It’s a wonderful way to discover Maine’s creative side beyond its renowned craft beer scene.
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Camp Manitou
While Camp Manitou is a private boys’ summer camp and not directly open to the public for visits, its presence on the shores of Great Pond profoundly shapes the character and history of Oakland. Established in 1924, it’s one of Maine’s oldest and most respected summer camps, a testament to the region’s enduring appeal as a summer retreat. You can appreciate its significance by understanding the vibrant summer camp culture that thrives in Maine, contributing to the local economy and instilling a love for the outdoors in generations of campers.
While you can’t walk through its grounds, you can experience the same stunning natural environment that draws campers here by exploring public access points on Great Pond. Consider renting a kayak or paddleboard from a local outfitter and venturing onto the lake yourself, experiencing the tranquility and beauty that defines the camp’s setting. It’s a reminder of the deep connection between Oakland and its pristine natural surroundings, offering a glimpse into a cherished part of Maine’s heritage. This appreciation of the camp’s role is perfect for those interested in local history, education, or simply enjoying the Great Pond’s beauty from public areas.
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Mount Phillip Trail
For a refreshing dose of nature and stunning panoramic views, the Mount Phillip Trail is an absolute must-do for outdoor enthusiasts visiting Oakland. This moderate hiking trail, located just a short drive from the town center, offers a rewarding ascent to the summit of Mount Phillip, providing breathtaking vistas of the surrounding lakes region, including Long Pond, Great Pond, and Messalonskee Lake. You’ll wind your way through a beautiful mixed forest, with the sounds of birdsong accompanying your steps.
The trail is well-maintained and marked, making it accessible for most fitness levels, though some sections are steeper. It’s an ideal activity for families seeking an active outing, couples looking for a romantic viewpoint, or solo travelers desiring a peaceful communion with nature. As you reach the top, the expansive scenery unfurls before you, a patchwork of shimmering water, lush greenery, and distant mountains. This trail is particularly spectacular in the fall when the foliage bursts into a riot of color, but it offers beauty in every season.
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Winterberry Farm
Immerse yourself in the charming world of sustainable agriculture and rural life at Winterberry Farm, a truly authentic Maine experience. This working organic farm offers visitors a unique opportunity to connect with the land, its animals, and the passionate people who cultivate it. You’ll find yourself wandering through fields of vibrant produce, visiting friendly farm animals like goats, chickens, and perhaps even a majestic draft horse, and learning about the farm’s commitment to organic practices and community engagement.
Depending on the season, you might be able to pick your own berries or pumpkins, adding a hands-on element to your visit. The farm often hosts seasonal events, workshops, or a farm stand selling their fresh produce, eggs, and homemade goods. It’s a wonderful educational outing for families with children, a peaceful retreat for couples, and an insightful stop for anyone interested in local food systems and sustainable living. The atmosphere is genuinely heartwarming, filled with the simple joys of farm life.
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Railroad Square Cinema
Just a short drive from Oakland, in the heart of Waterville, you’ll discover the Railroad Square Cinema, a beloved independent movie theater that’s a cultural cornerstone of the region. This isn’t your typical multiplex; Railroad Square prides itself on showcasing a diverse selection of independent films, foreign cinema, documentaries, and art-house features that you won’t find anywhere else. You’ll step into a cozy, intimate setting, often with a vibrant community feel, where film lovers gather to enjoy thoughtfully curated cinematic experiences.
Beyond its regular screenings, the cinema is a key venue for the Maine International Film Festival, transforming into a buzzing hub of film activity each summer. It’s an ideal spot for couples on a date night, solo cinephiles seeking an inspiring film, or anyone looking to support local arts and culture. Attending a screening here offers a truly authentic and enriching evening out, reminding you of the power of independent storytelling.
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Mainely Escapes
For an exhilarating and brain-teasing adventure, look no further than Mainely Escapes, located conveniently in nearby Waterville. This isn’t just an activity; it’s an immersive experience that challenges your mind and teamwork skills. You and your group will be locked in a themed room, tasked with solving a series of puzzles, riddles, and challenges to “escape” within a set time limit, usually 60 minutes.
Imagine deciphering cryptic clues, unlocking mysterious boxes, and working collaboratively to piece together a story, all while the clock ticks down. Each room has a unique narrative and intricate design, transporting you to a different world, from a fantastical quest to a thrilling mystery. It’s an incredibly engaging activity that fosters communication and problem-solving, making it perfect for families with older children, groups of friends, corporate team-building, or even a unique date night. You’ll leave feeling accomplished and buzzing with excitement from the adrenaline rush.
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Colby College Museum of Art
Just a stone’s throw from Oakland, on the beautiful campus of Colby College in Waterville, lies the Colby College Museum of Art, a true cultural gem and one of Maine’s premier art institutions. This museum offers an impressive and diverse collection, ranging from ancient to contemporary art, with a particular strength in American art, including significant works by prominent artists like Alex Katz and John Marin. You’ll wander through spacious, thoughtfully curated galleries, encountering masterpieces that provoke thought and inspire awe.
The museum also hosts compelling rotating exhibitions, ensuring there’s always something new to discover with each visit. It’s a serene and intellectually stimulating environment, perfect for art lovers, students, or anyone seeking a moment of quiet contemplation and cultural enrichment. Best of all, admission is free, making world-class art accessible to everyone. Allow yourself to be captivated by the beauty and stories held within these walls.
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Maine International Film Festival
If your visit to Oakland aligns with July, you are in for a cinematic treat with the Maine International Film Festival (MIFF), primarily centered in nearby Waterville. This acclaimed festival transforms the quiet city into a buzzing hub of film enthusiasts, filmmakers, and industry professionals. You’ll have the incredible opportunity to screen a diverse selection of independent films from around the world, many of which are premieres, alongside classic cinema and thought-provoking documentaries.
Beyond the screenings at Railroad Square Cinema and Colby College, MIFF offers Q&A sessions with directors and actors, panel discussions, and lively social events, creating an immersive and interactive experience. It’s an unparalleled opportunity to delve deep into the world of film, discover new talent, and engage in meaningful conversations about storytelling. This festival is a must for film buffs, aspiring filmmakers, and anyone seeking a unique cultural event that brings global cinema to rural Maine.
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Waterville Country Club
For golf enthusiasts visiting Oakland, the Waterville Country Club offers a superb opportunity to hit the links on a beautifully maintained course just a short drive away. This classic 18-hole championship course, established in 1926, is renowned for its challenging yet fair layout, featuring rolling fairways, strategically placed bunkers, and pristine greens. You’ll enjoy a round amidst scenic New England landscapes, with mature trees lining the fairways and glimpses of the surrounding countryside.
The club offers a full range of amenities, including a pro shop, practice facilities, and a welcoming clubhouse with dining options, perfect for relaxing after your game. Whether you’re a seasoned golfer looking for a competitive round or a casual player seeking a pleasant afternoon on the course, Waterville Country Club provides a memorable experience. It’s an ideal outing for golf-loving couples, groups of friends, or solo players looking to enjoy Maine’s outdoor recreational offerings.
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Waterville Opera House
Experience the grandeur and cultural vibrancy of the Waterville Opera House, a historic performing arts venue located in the heart of Waterville, just minutes from Oakland. This beautifully restored theater, dating back to 1902, is a true architectural marvel, boasting stunning Victorian-era details and excellent acoustics. You’ll be transported to a world of captivating performances, from Broadway touring productions and live music concerts to local theatrical productions and comedy shows.
The Opera House hosts a diverse calendar of events throughout the year, ensuring there’s always something to entertain and inspire. Attending a show here isn’t just about the performance; it’s about stepping into a piece of local history and supporting the vibrant arts scene that enriches central Maine. It’s a perfect evening out for couples, families (depending on the show), or solo travelers looking for a dose of culture and entertainment. Check their schedule and plan your visit around a performance that catches your eye.
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Old Western Fort
Embark on a fascinating journey back in time to the 18th century at Old Fort Western, a National Historic Landmark located in nearby Augusta, Maine’s capital city. This isn’t just a collection of old buildings; it’s the oldest surviving wooden fort in New England, built in 1754 during the French and Indian War. You’ll step onto the very grounds where soldiers, traders, and settlers lived and worked, experiencing firsthand what life was like on the Maine frontier.
Explore the original fort building, barracks, and store, filled with authentic artifacts and period furnishings. Knowledgeable interpreters often provide engaging tours and demonstrations, bringing history to life with stories of military life, trade with Native Americans, and the challenges of colonial settlement. It’s an incredibly educational and immersive experience, perfect for history buffs of all ages, families, and anyone curious about Maine’s pivotal role in early American history.
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Maine State Museum
Continue your historical and cultural exploration with a visit to the Maine State Museum, also conveniently located in Augusta. This expansive museum offers a comprehensive and engaging look at Maine’s rich natural and cultural heritage, from its geological origins to its vibrant industrial past and diverse communities. You’ll wander through fascinating exhibits showcasing everything from prehistoric artifacts and native wildlife dioramas to displays on Maine’s shipbuilding, logging, and agricultural industries.
Imagine seeing a full-scale logging camp, exploring a recreated 19th-century village, or marveling at exquisite examples of Maine craftsmanship. The museum does an excellent job of bringing history to life through interactive displays and detailed narratives, making it enjoyable for visitors of all ages. It’s an ideal destination for families, history enthusiasts, and anyone wanting to gain a deeper understanding of the Pine Tree State’s unique identity.
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The State Capitol
Complete your visit to Maine’s capital by exploring The State Capitol building in Augusta, an iconic landmark that embodies the state’s governance and history. Designed by renowned architect Charles Bulfinch and completed in 1832, this impressive granite structure stands majestically atop a hill overlooking the Kennebec River. You can take a self-guided tour or, when available, join a guided tour to learn about the building’s architecture, its historical significance, and the workings of Maine’s legislative process.
Wander through the Hall of Flags, admire the grand staircase, and peek into the legislative chambers (when not in session). It’s a fantastic opportunity to witness the heart of Maine’s government and appreciate the democratic process. This visit is perfect for history buffs, civics enthusiasts, or anyone interested in architecture and public service. It offers a tangible connection to the state’s past and present, providing a fitting conclusion to your exploration of the region.
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Plan Your Visit
As you can see, Oakland, Maine, and its vibrant surrounding region offer an incredible tapestry of experiences waiting to be discovered. From the tranquil waters of Great Pond and the invigorating trails of Mount Phillip to the rich history of Old Fort Western and the thriving arts scene in Waterville, this central Maine gem truly has something for everyone. You’ll find yourself indulging in farm-fresh delights, savoring unique local spirits, immersing yourself in captivating performances, and connecting with the authentic spirit of the Pine Tree State.
It’s a destination that promises both peaceful escapes and exciting adventures, all wrapped in quintessential New England charm. So, what are you waiting for? Start planning your Oakland getaway today! Pack your bags, set your GPS, and prepare to create unforgettable memories in a place where natural beauty, cultural richness, and genuine hospitality converge. Your Maine adventure awaits!
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