15 Best Things to Do in Oakland (Maine)

Often referred to as the ‘The Gateway to the Belgrade Lakes Region,’ Oakland is in Maine’s Kennebec County and was first settled in the 1780s.

Before it was settled by English colonists, the area was named Taconnet, after a local Native American chief.

The town lies about twenty miles north of the state capital Augusta, and just a few miles from the larger town of Waterville.

Central Maine’s Belgrade Lakes are premiere recreation destinations for the state’s residents and provide a variety of outdoor activities year-round.

Below are 15 things to see and do in and around Oakland, Maine.

1. Riverside Farm Market and Café

For a meal with a view that’s straight off the canvas of a Winslow Homer painting, consider stopping at Riverside Farm Market and Café on Fairfield Street in Oakland.

Its idyllic views include pastures, ponds, and a vineyard, which are especially lovely when viewed from the café’s outdoor seating area.

The café has a tantalizing menu that includes soups, salads, and sandwiches, to name a few. Most of the dishes are made with local, seasonal ingredients.

There’s a small farmer’s market on site as well that’s well-stocked with wine and other prepared food and bakery items like cookies and cheese.

2. Snow Pond Cruises

Though its real name is Messalonskee Lake, it’s no wonder that with all those syllables, local folks generally refer to it as Snow Pond.

With a shoreline stretching for nearly 30 miles, it may be more of a lake than a pond, but either way, it’s a nature-lovers paradise, and hands down the best way to take in its splendor is by boat.

Boat tours kick-off at Rocky Shore Lane in Oakland, and afternoon tours that include the sunset are among the most popular.

Consider bringing a bottle of bubbly, a loaf of French bread, and a hunk of local cheddar and having a picnic.

3. Tree Spirits Winery and Distillery

Located just a hop, skip, and jump off Interstate 95, Tree Spirits Winery and Distillery is conveniently close to other area attractions, making a great side-excursion and efficient use of valuable vacation time.

They produce a wide variety of wines and spirits onsite, including brandy and absinthe – a mystical green liquor infused with fennel and black licorice that was once thought to give drinkers strange hallucinations.

Many of their most popular wines are fruit-infused, so stop by and peruse their wide variety of products and sample a few to see which you prefer before buying.

They’re located on Fairfield Street in Oakland.

4. Camp Manitou

For nearly 70 years, Camp Manitou in Oakland has been hosting summer camps for boys from the age of 7 all the way up to 16.

Located in the heart of the Belgrade Lakes Region, it is one of the oldest and most recognized establishments of its kind in the entire country.

The camp is staffed with professional teachers and coaches, many of whom have been working at the camp for years.

Idle time isn’t something that anxious parents need to worry about, as the camp’s schedule is packed with calorie burning and character building activities designed to excite, engage, and educate children.

Check out their website for specific camp information.

5. Mount Phillip Trail

Nearby Rome, Maine is home to one of the area’s most popular hiking trails.

With a change in elevation of nearly 400 feet, the apex of the Mount Phillip Trail will give visitors a picturesque view of many of the region’s lakes, some of which stretch to the horizon and can be seen clearly on a cloudless day.

There’s adequate parking at the trailhead, and the trail itself is well-marked, so you won’t need to drop breadcrumbs. For those in relatively good physical shape, the hike should take about an hour one way.

The trail is appropriate for children, but not those confined to a stroller.

6. Winterberry Farm

Just off Route 27 in Belgrade, Maine, Winterberry Farm is comprised of 40 acres dedicated to producing a variety of certified organic products.

The farm’s home was originally built in the late 1800s, and in addition to the working farm, there’s also a market that’s chock-full of healthy, all-natural produce and prepared food items.

Farm tours are available for groups, but you’ll need to let them know that you’re coming in advance. They even offer children’s camps and farm stays for those interested in a total immersion experience.

The children’s summer camp includes lots of quality time with the farm’s friendly animals.

7. Railroad Square Cinema

Located in the Railroad Square in Waterville, the Railroad Square Cinema was initially opened in the ‘70s, but rumor has it that back then it wasn’t a particularly inviting venue.

Since then, the cinema has undergone a few rounds of renovation and is now one of the area’s most popular movie destinations.

They show an eclectic mix of classic and contemporary movies, many of which you won’t see at the larger commercial theaters.

All things considered, the tickets are pretty inexpensive, and catching a movie or two is a great way to spend a few hours, especially when the weather isn’t conducive to outdoor activities.

8. Mainely Escapes

Even for those who’ve never experienced a New England winter, it probably won’t come as a surprise that the weather can be frigid, icy, and even dangerous.

When that’s the case, it’s great to have a few indoor activities in your back pocket, and escape rooms are just the thing.

Located on Main Street in Waterville, Mainely Escapes has a variety of rooms, each with its own unique theme. Some are appropriate for groups that include children.

Escape rooms are fun, relatively inexpensive, and give guests a unique sense of urgency and suspense that you just don’t find in many other forms of recreation.

9. Colby College Museum of Art

Free activities are golden, especially for vacationers whose travel dollars are disappearing at an alarming pace.

The Colby College Museum of Art is located on Mayflower Hill Drive in Waterville and is one of those rare gems that usually far exceeds the expectations of those who take the time to visit.

Much of their art is produced by local and regional artists and includes iconic New England themes like seascapes and lighthouses.

The museum is larger and more complete than many college art museums, and there’s a café on site that’s a great place to relax and regroup before heading off on your next adventure.

10. Maine International Film Festival

Maine’s International Film Festival is one that’s gaining in popularity and nationwide recognition.

Taking place over ten days in July, it is conveniently located in Waterville, just down the road from Oakland.

In addition to the dozens of movies across all genres that will be officially released, the festivities include live music and theater performances, exhibitions, and a variety of workshops and instructional courses aimed at folks interested in the visual arts.

Lots of producers, screenwriters, actors, and actresses will be on hand too.

It’s an interesting slice of an industry that most of us only ever get to see from a seat in a crowded movie theater.

11. Waterville Country Club

With its incredible natural scenery and usually perfect spring and summer weather, Maine is a natural fit for golfers; Waterville Country Club is an 18-hole course that’s one of the most popular in the area.

It’s full of changes in elevations, treed areas, and water and sand hazards that make it scenic and challenging.

The club is considered semi-private, which means that full-members get the first crack at tee times during peak season. But don’t worry, one-time guests aren’t excluded. The course features a restaurant, pro shop, putting greens, and a practice range if you’d like to hit a few to warm up before tee time.

12. Waterville Opera House

For nearly five decades, the Waterville Opera House has been a valuable community resource providing an inexpensive means of recreation usually only found in larger metropolitan areas.

Founded in 1975, they provide a variety of live entertainment options in addition to opera, including live music, theater, and even stand-up comedy.

It’s a genuinely diverse venue that’s retained much of its quaint charm, even though it boasts state of the art facilities.

They’re open year-round, so check out the calendar of events on their website to see what’s on the schedule for when you plan on being in town.

13. Old Western Fort

Located in Augusta, the capital of Maine, Old Western Fort is a premier destination for those looking for a fascinating insight into the region’s history, that’s older than nearly any other place in the country.

The Old Western Fort was initially built in the mid-1700s and is the oldest nearly-original wooden fort of its kind.

The site is open seasonally, and guided tours are available for those who want that extra bit of value that’s well worth the price.

Admission is inexpensive, and children’s admission is cheaper than adults, so don’t leave anyone behind; it’s the kind of place that is interesting, educational, and engaging for adults and children alike.

14. Maine State Museum

There’s cheap admission, and then there’s really cheap admission, and luckily, the Maine State Museum falls into the second category, meaning that a typical family of four can get in for less than the cost of a Happy Meal.

One of the state’s most complete collections of all things historical, many of the items on display are original pieces dating back hundreds of years.

Weapons, clothes, historical documents, and housewares are a few of the things you’ll see; nearly all of them include signs that explain what you’re seeing and why it’s significant.

There are interesting exhibits on the natural world in addition to history.

15. The State Capitol

Located in historic downtown Augusta, Maine’s State Capital building was built in the 1820s and is open to tours year-round.

There’s no cost to take a tour, but you must sign up in advance, and many guests have mentioned that their experience far exceeded their expectations, which isn’t usually the case for free activities.

The capitol is a well-appointed and meticulously restored building that includes a variety of historical exhibits and a gallery full of original paintings of most of the state’s previous governors.

Tours typically take an hour or so and are even appropriate for families with young children.