Cumberland, Maine: The Cumberland Fair, Casco Bay, and a Classic New England Town

Just north of Portland, the town of Cumberland blends country and coast in classic Maine fashion. It is best known for its beloved agricultural fair, but it also has a shorefront on Casco Bay, working orchards, and a wonderful network of preserves and trails. Here is a guide to Cumberland, Maine, and its village center.

A Town of Three Villages

Cumberland sits in Cumberland County, about 11 miles northeast of Portland. Settled back in the 1600s and long a farming community, it split from neighboring North Yarmouth to become its own town in 1821. Today it is home to roughly 8,000 residents and is really made up of three distinct areas: Cumberland Center, the government-and-schools hub in the geographic middle of town; Cumberland Foreside, the coastal side along Casco Bay; and West Cumberland. Cumberland Center serves as the village heart, with its churches, schools, and small-town charm.

The Cumberland Fair

The town’s signature event is the Cumberland Fair, one of Maine’s classic agricultural fairs, held here every September since 1868. For more than 150 years it has drawn crowds for harness racing, ox and horse pulling, livestock and agricultural competitions, horticulture and giant-pumpkin contests, a midway of rides, and, of course, all the fair food you can eat. It is a cherished New England autumn tradition and the highlight of the local calendar.

Farms and Orchards

Cumberland keeps its agricultural roots alive. While only a handful of working farms remain, local favorites like Sweetser’s Apple Barrel & Orchards and Double T Orchards keep the harvest tradition going — and make Cumberland a fine spot for fall apple picking in Maine. Farm stands and orchards here are at their best in September and October, right around fair time.

The Great Outdoors

For such a small town, Cumberland offers an impressive amount of green space. The Twin Brook Recreation Area, near the town center, has miles of trails for walking, running, and mountain biking, plus disc golf and cross-country skiing in winter. Beyond it, residents and visitors enjoy the Town Forest, Rines Forest, Knight’s Pond Preserve, and the Val Halla golf course — a network of well-loved outdoor spaces for every season.

The Casco Bay Coast

Cumberland Foreside faces the island-studded waters of Casco Bay, where shorefront spots like the Broad Cove Reserve offer lovely views and quiet walks. The bay has long shaped the town: Chebeague Island, out in Casco Bay, was part of Cumberland for generations before it became its own town in 2007. Nearby islands like Cousins Island give a taste of the classic Maine coast just minutes away.

History and Landmarks

Cumberland wears its history well. The handsome Cumberland Congregational Church anchors the village center, the Greely schools have long served the community, and the Cumberland Historical Society preserves the town’s stories and old homes. A stroll through Cumberland Center reveals the graceful architecture and unhurried pace of a well-kept New England town.

Exploring the Area

Cumberland’s location makes it a comfortable base for the greater Portland area, close to Yarmouth, Falmouth, and the city itself, with easy access to the coast. Travelers exploring southern and central Maine often pass through the Kennebec Valley; our own town of Winslow, with its colonial-era Fort Halifax, shares in the long story of Maine’s river-and-coast communities.

Frequently Asked Questions