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Cumberland Food Stop

How To Spend a Day in Cumberland, Maine? (2024)

One of the largest towns in Maine, Cumberland is reportedly the safest place to settle in and around Maine. This community-oriented town is a part of the Portland metropolitan area and is also Maine’s one of wealthiest municipalities. Not only for its proximity to the popular Portland but Cumberland is also known for being a town close to the Canadian- U.S. Border. What appeals to settlers towards Cumberland is its hospitality, friendly locals, fresh air, cleanliness, and tranquility, that too within proximity with such a humungous metropolitan “Portland.”

Though not only amongst post-retirement settlers, this lovely little idyllic town in Southern Maine is also popular amongst travelers. The slow summer living, wooded spread, charmingly expansive farmland, and recreational opportunities have always kept Cumberland as a tourist hotspot. From nearby cities like Portland, Kennebunkport, Cape Elizabeth, and more, Cumberland makes a charming weekend getaway or a day trip destination. Getting into secluded nature away from the vacation crowd is Cumberland’s’ USP, and everyone should choose to enjoy the same. So, are you ready?

How To Spend a Day in Cumberland, Maine?

Join us to find out Things to do in Cumberland for a day or weekend trip. Have a look:

1. Have Fun at the Twin Brook Recreation Area

Undoubtedly one of the best things to do in Cumberland is spending some time at the Twin Brook Recreation Area. This 224-acre of landscape spread is basically a four-season park where both locals and tourists gather for recreational purposes. The park is open to several non-motorized outdoor activities, but still, it rarely gets overcrowded. Twin Brook is open year-round and is home to four miles of nature walking trails, a disc golfing ground, 22 acres of mixed athletic fields, and several sports fields, including softball, baseball, soccer, and a lot more. During the winter months, several trails at Twin Brook are groomed for fun activities like snowshoeing and cross-country skiing. You can also find locals flying kites or enjoying an afternoon picnic on most days here. Twin Brook is also popular for its photogenic red barn, where people gather for photographing opportunities.

2. When in Cumberland, You Cannot Miss Trying Needhams at Cumberland Food Stop.

If you are in for some good quality food, snacks, and drinks in Cumberland, then do check out the Cumberland Food stop. This dynamic shop has been in the town since 1998, and since then, it has only entertained and satisfied food enthusiasts. This very quaint, no-frills local watering hole is located within the town’s central location right across quaint Greely High School street. It is where kids, youths, adults, and retirees gather alike. Cumberland Food stop has everything from Wine, Craft Beer, Grocery, Grab and Go, along with other options. Though what they are extremely popular for are their Sandwiches, Paninis, Pizza, Burgers, Wraps, Salads, the iconic ‘Stop Sauce,’ and more. It is also an excellent place to try Needhams, a confectionery dessert bar associated with Maine since 1872. Since Needhams are hard to find outside Maine, make sure you try them when in Cumberland.

3. Get Historical at the Cumberland Historical Society.

Cumberland Historical Society is a non-profit organization that aims to collect and preserve artifacts that speak about Cumberland’s history as a town. This premier history and education center has its headquarters in the old Cumberland Schoolhouse. The society also comprises a library, education center, museum shop, and photo archives, along with the Two Mile House. The collection of artifacts ranges from old black and white pictures, wooden furniture that never came in use, records and manuscripts, folk art, and books. 

The Cumberland Historical Society also organizes walking tours, family-oriented programs, workshops, bus trips, and more such events for engaging, educating, and entertaining the public.

4. Check Out the Broad Cove Reserve

Broad Cove Reserve is a beautiful 23 acres of beachfront property and a popular place to visit in Cumberland. The reserve features a short Stonewall Trail, a small beach, a pair, and numerous walking paths. Operating sunrise to sunset 7 days a week, Broad Cove is owned by the town and some locals, but it always welcomes visitors for free. During the summer months, one can enjoy a range of activities like swimming, picnicking, fishing, kayaking, paddle boating, and more. Whereas during winters, the Broad Cove Reserve allows visitors to enjoy some low-key snow Skiing experience. Broad Cove Reserve also has an interesting history since it was once the fishing ground for the Abenaki people.

The property also allows dogs, though only to the pier and definitely not on the beach.

5. Get Towards Cumberland’s Other Outdoor Landscape, The Knight’s Pond Preserve.

Knight’s Pond Preserve is a natural preserve in Cumberland and North Yarmouth. Basically a public park, it is located within a mile from the town centers of both Cumberland and North Yarmouth. The preserve features a gorgeous, glassy, deep blue 46-acre pond that has a scenic old-growth forest in the surroundings. In addition, the preserve is also home to some critical wildlife habitats, a huge forestland, a network of six miles of trails, and adventure. Visitors can enjoy a range of activities like nature walking and hiking, kayaking, kids camping, bird watching, soaking under the sun, fishing, hunting, ice skating, and snowmobiling. Knight’s Pond Preserve is also an excellent location popular amongst photography enthusiasts. Everything here, from the dense canopy of oaks too the lake full of lily pads and fluttering dragonflies and other mesmerizing views of nature, bring in some excellent picturesque opportunities.

6. If it is September, Then Attend The Annual Cumberland Fair.

The Annual Cumberland Fair is an over 150-year-old tradition that celebrates and brings the agricultural sector into the limelight. Organized every year in the last week of September, it is one of the biggest fairs in Maine and, therefore, a must-visit. Cumberland Fair includes everything from a petting zoo, carnival rides, pig races, and pumpkin weigh-offs, along with some fine dining and munching possibilities. The event begins with farmers showing off their cattle and is followed by the cooking and needlework skills of the locals. You will likely witness Maine State Pumpkin, and when you see the giant pumpkin, do not forget to make a wish. Farmers can bring their pumpkins, and the winner gets $500 prize money. Back in 2015, Edwin Pierpont, a local farmer, brought a gigantic 1,046-pound pumpkin that’s still the biggest this event saw.

7. Dine at Dara Bistro

Formerly known as the Cumberland Food Company, Dara Bistro is a very welcoming and warming dining space in Cumberland, Maine. During daylight hours, it is a casual coffee shop, but as it sunsets, it transforms into a formal dining space. Dara Bistro is located right in the center of the town in the woodlands near a local cemetery. It has an old historic charm similar to that of a massive, renovated barn. Dara Bistro features both indoor and outdoor dining. It specializes in Southern-style comfort food, and its menu changes continuously with the seasons. When here, do try Pineland Farms Bean Salad, Chef Bryan Dame’s grandmother’s bread-n-butter pickles, and Country Pork Terrine & Rillette. For a quick grab-and-go, their Bacon Egg and Cheddar Sandwiches and Fruit n’ Granola bowls are quite a trend. And forget not; the coffee here will undoubtedly leave you impressed.

8. Visit Sunflower Farm Creamery and Watch Nigerian Dwarf Goats.

Nigerian dwarf goats are just like the American Pygmy Goat, and you must check out them when in Cumberland. Sunflower Farm Creamery is basically the place where you can meet and pet these goats, indulge in goat yoga, and buy back several goat dairy products. Goat Yoga is undoubtedly one unique experience (where goats interact with the yogis or even climb upon), and when in this creamery, you cannot miss it. This weird yoga trend happens twice a week, and in recent years, it has gripped the locals of Maine quite profoundly. If not, one can visit the creamery to buy items like goat milk ricotta, chocolate chip cookie chevre ice cream sandwiches, milk feta, goat milk caramels, chipotle lime & chive chevre, vanilla goat milk yogurt, and more.

9. During the Riping Season, Do Visit Sweetser’s Apple Barrel and Orchards.

One of the most popular things to do in Cumberland is visiting the Sweetser’s Apple Barrel and Orchards. From late summer through the fall season, this longstanding family orchard operates some gems of experiences. They grow 50 apple varietals which visitors can pick on their own. The varieties range from names you may not have heard before to the obvious ones. They have Ben Davis, Blue Pearmain, Northern Spy, Duchess, Pound Sweet, Gala, Golden, and much more. The Maine-y “Snowapple” McIntosh, Honeycrisp, and “Wealthy” apples are some classics you cannot miss. While some apples start riping from the month of August, the classic apple-picking season though starts in September and October. The Orchard also has flowers, maple syrup, pumpkins, honey, selective vegetables, cider donuts, fresh-baked apple pies, pastries, apple butter, apple cider, and more.

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