7 Best Things to Do in Oakland, Maine (2024)

Oakland is located in Kennebec County and is one of the safest towns to reside in in Maine. Its low crime rates, low taxes, excellent schools, and plenty of recreational opportunities make it a wonderful place to be at. The population of Oakland is though less than 6500; what raises the crowd here are those year-round tourists. For an authentic small-town vacation in Maine, Oakland is an ideal destination, and people swear by that. Also referred to as the Gateway to the Belgrade Lakes Region, Oakland has so much to do.

Oakland was initially named after Taconnet, a local Native American chief. Later it was settled by English colonists and got the name Oakland. This tiny town is within proximity to Maine’s capital Augusta just 20 miles north of it. In addition, it is just 5.1 miles from Maine’s other small town, Waterville. Wondering what a day trip or weekend vacation to Oakland would look like? Well, here is a list of all the Popular Things to Do in Oakland, Maine. Have a look:

7 Best Things to Do in Oakland, Maine

1. Try Out The Tree Spirits Winery and Distillery

Visiting the Tree Spirits Winery and Distillery is one of the best things to do in Oakland. This winery and distillery have a tasting room in Oakland, a short walk off I-95 at exit 127 or 130. It is conveniently close to tourist attractions and major destinations like Colby College and the Colby Museum of Art. Tree Spirits Winery and Distillery in Oakland offers a wide range of wines, spirits, and beers. Some of the popular drinks one must try here include brandy, absinthe, and fruit-infused wines. Absinthe at Tree Spirits is basically green liquor infused with fennel and black licorice, something hard and exciting for regular wine lovers. In addition, they also have a range of sublimes options, a must-try. Tree Spirits offer a wide variety of products and samples to try before visitors actually decide on what they want to buy. Apart from popular adult drinks, the facility also sells apple cider, pear cider, and maple syrup sourced from nearby production facilities.

2. Tour With Snow Pond Cruises

Touring with Snow Pond Cruises is undoubtedly one popular thing to do in Oakland. The Snow Pond Cruises run on Messalonskee Lake and allow participants to explore the mesmerizing lake’s beauty. This excellent 3-hour-long cruise kick-off at Rocky Shore Lane in Oakland. Amongst the multiple tour options, the afternoon tour featuring sunset views is definitely the most exciting one to choose from. Capt Gary, the guide on board, has excellent local knowledge and unwinds hilarious stories that make the experience more exciting. The cruise boat is quiet and comfortable and even allows pet dogs onboard. However, participants must take care of their pet’s safety since boat boundaries aren’t very high. Messalonskee Lake, or as they lovingly call it, ‘Snow Pond,’ is a nature lover’s paradise for sure.

3. Visit Winterberry Farm With Friends and Family

Winterberry Farm is located right off Route 27 in Belgrade, less than 10 miles from Oakland. The farm was built back in the late 1800s and covers 40 acres of land, all of which are used for certified organic farming. The management staff at Winterberry offers farm tours for groups. However, for a tour here, one has to inform well in advance. If not, visitors can still check out the adjacent market that is all about healthy, all-natural produce and prepared eatables. In addition to a working farm and fresh produce market, Winterberry Farm is also popular for its children’s camps, and farm stays. These experiences are undoubtedly hypnotic, and kids love living them to the core.

4. Hike the Mount Phillip Trail

The Mount Phillip Trail in Rome, 12 miles outside Oakland, calls for a fun daytime hike. This moderately challenging, 1.3 miles loop trail is ideal for both beginners and experts. The Mount Phillip Trail makes its way through mature stands of pines and hemlock. After gently climbing through the forest and Greenland route, the trail takes hikers to a rocky ledge on the eastern side of Mount Phillip. Upon reaching here, hikers can witness the beautiful views of Kennebec Highlands to the west and Great Pond to the south. The trail then descends to the west, and after dropping down to mature hemlocks, it makes its final way to the parking lot.

5. Take Your Young Boys To Camp Manitou.

Camp Manitou is a popular summer camp in Oakland for boys aged between 7 to 16 years. This summer camp has been running since 1947 with the aim of helping boys in becoming leaders. It, in fact, is one of the oldest and most recognized camps in the entire United States. Camp Manitou has professional coaches and teachers with years of experience and certified services. The camp is packed with different learning and engaging activities from art, and craft, science, sports, nature, and a lot more. Not just that but the camp also focuses on physical and mental fitness and character building for every participant. No games, videos, and other such entertainment stuff are allowed in the camp since the staff here believes in connecting kids with real and natural resources of fun.

6. Visit the McCartney House Museum

Mc Cartney House Museum is a small museum in Oakland, Maine. This historical museum was one of Oakland’s oldest homes and was built back in 1815 by Leonard Cornforth. The museum is named after its primary owners, the Macartney Family, who grew up three generations here. The home structure is one fine example of a Federal-trimmed Cape Cod, a blend of styles popular about 1815 in Oakland. Several changes have been made over these years, but nothing to destroy the original appearance of the building. Inside the MC Cartney House is a parlor room, a dining room, and one keeping room. Moving upstairs is a costume room and an office room. There’s also a period garden outside featuring flower trees, some of which have been here since the 1900s. For a history and old home lover, this museum is a must-visit in Oakland.

7. For a Quick Meal, Visit The Korner Store and Deli.

The Korner Store and Deli in Oakland offers a large selection of food and beverages. Owned by a family since 1983, the Korner Store is conveniently located at 45 Oak Street. The shop is known for its Special sandwiches and the mouthwatering Lobster Roll. If that isn’t the food choice for you, they also have a variety of burgers, pizzas, salads, breakfast baskets, and platters, along with wraps and quesadillas. Korner Store and Deli also deliver all across Oakland Monday through Saturday, 11 am to 8 pm. However, their in-house dining/ purchase is open from Monday through Friday, 7 am to 9 pm, and on Saturdays, 8 am to 9 pm. The store remains closed on Sundays.