Welcome to Westbrook & the Lakes Region

Located northwest of Portland, Westbrook and the Lakes Region has plenty of four-season fun on scenic trails, lakes and rivers. Area farms are ready for apple harvesting and pumpkin picking, and farm stands are full of pies. Explore downtown Westbrook along the Riverwalk, with a stop at Black Dinah Chocolatiers, or go country with a hike up Hacker’s Hill or a seaplane adventure followed by live music over a burger and beer at Erik’s Church or Lenny’s.


1. Run the Ridge

This trail and mowed-path course should be bursting with autumn colors for the Oct. 20 races at Sunset Ridge Golf Course in Westbrook. The three race options are 5K, 10K and a K9 5K (run with your dog!). This event benefits Discover Downtown Westbrook, to support their mission of economic and community revitalization in downtown Westbrook. Registration is $25/$30 on race day. (

2. Westbrook Riverwalk

The Westbrook Riverwalk, which runs parallel to Main Street from Cumberland Street to Bridge Street, offers a chance to take in a little of Westbrook’s history while stretching your legs. Stroll past the powerful Saccarappa Falls and historic Dana Warp Mill and through downtown to Riverbank Park. Parking is available at numerous free parking lots along Main Street.

3. Black Dinah Chocolatiers

Black Dinah Chocolatier. Photo by Shannon Bryan

Black Dinah Chocolatiers, a nationally recognized maker of gourmet chocolate truffles, has a small tasting room and factory in the Edwards Block building at 869 Main St. (Suite 500), Westbrook (the same building as Portland Pie). Stop in and bang the gong in the showroom to let them know they have visitors. Free tours are available with advance registration: 207–887–9763 or

4. Lenny’s at Hawkes Plaza

Lenny’s at Hawkes Plaza. Photo by Derek Davis/Portland Press Herald

Lenny’s serves up sensibly sourced homestyle food along with some of Maine’s best roots music performers. If you’ve been coming to the Lakes Region forever, you know the iconic Hawkes TV repairman sign with the swinging arm on Route 302. That’s where Lenny’s is: 1274 Bridgton Road (Route 302), Westbrook. They’re open Tuesday through Saturday, 3:30–10 p.m. (food served 5–9 p.m.) and Sunday 3–8 p.m. (food served 4–7 p.m.). For the latest on performers:

5. Randall Orchards

Fall weather means apple picking season in Maine, and Randall Orchards is one of the most well-known in the area. The farm and orchard in Standish has been in operation since 1906 and is 15 minutes from Portland off Route 25 at 1 Randall Road in Standish. October means many varieties of apples, pumpkins and squash, and a working cider mill. (207–642–3500)

6. Ghost Hunt at (Haunted?) Old Red Church

Join the Maine Afterlife Research Society for a spooky good time investigating the Old Red Church at 55 Oak Hill Road in Standish. See what it’s like to be a paranormal investigator while searching what is thought to be one of Maine’s most haunted locations. There are two sessions: Oct. 19 and Oct. 20, 7–11 p.m. Tickets are $20 and are limited. (

7. Erik’s Church

Swing on over to Windham’s newest hot spot, Erik’s Church, for a bite to eat, a cold drink and some country charm. There’s live entertainment every day at lunch from noon to 2 p.m. and live country music or karaoke just about every night; for the lineup, check The Church is at 824 Roosevelt Trail, Windham.

8. Triple B: Boots, Band & BBQ

Join Riding to the Top for a down-home night of BBQ, dancing to Under the Covers, a Best Boots contest and an auction to benefit therapeutic riding programs. The party is at 14 Lilac Drive in Windham, and tickets are $50 available through Eventbrite (look for “11th Annual Triple B ~ Boots, Band & BBQ”). Riding to the Top has provided therapeutic horseback riding services to thousands of children and adults with a wide range of physical, emotional and learning disabilities since 1993.

9. Hacker’s Hill

Hacker’s Hill. Photo by Amy Paradysz

Take in the 360-degree views of the White Mountains to the northwest, Maine mountains to the north and Sebago Lake to the southwest on top of Hacker’s Hill Preserve on Quaker Ridge Road in Casco. The preserve is open to the public, with a picnic area and bathroom at the top. Take Route 302 through Windham to the Casco town line, look for Cry of the Loon gift shop on the right and take a right onto Quaker Ridge Road. The hill is a few miles up on the right.

10. Naples Seaplane Adventures

Naples Seaplane Adventures. Courtesy photo

For a bird’s-eye view of the Lakes Region, make a reservation for a seaplane flight leaving from a dock on Long Lake in Naples. Naples Seaplane Adventures has a float plane that takes up to five passengers on flights starting at $45 per adult ($35 per child). (207–232–2594;