Jenna Hill, of South Portland, beams during a downhill stretch while cross-country skiing at Smiling Hill Farm. Ben McCanna/Staff Photographer

Five Fields Farm

720 South Bridgton Road (Route 107), South Bridgton

At an elevation of 850 feet, this apple farm is on the right side of the “snow line” for snowshoeing and skiers. The trail system starts at the back lawn and connects with logging roads and links with lands owned by abutters, including the Loon Echo Land Trust on Bald Pate Mountain. Trails are typically one way, with bi-directional skiing only where absolutely necessary. Groomed trails do not extend to the summit, but snowshoe hikers and adventuresome skiers regularly make the 20-minute back-country trek for a view to the horizon that, on clear days, includes Mount Washington. Trail fees are $12 for adults, $10 for kids, with discounts after 2 p.m. Open daily 9 a.m. to 5 p.m. Call (207) 647-2425.

Gilsland Farm

20 Gilsland Farm Road, Falmouth

This 65-acre Maine Audubon sanctuary, just five minutes from Portland, has 3.5 miles of gentle trails winding along a pond and through forest, meadow, orchard and salt marsh. Access is free, but you have to bring your own snowshoes or skis and leave your dog at home. The main trailhead is just outside the Education Center at the end of the driveway; from there, access all the trail spurs and junctions and the main trail loops. Trail details are available at For more information, call (207) 781-2330.


Harris Farm

280 Buzzell Road, Dayton

This 600-acre dairy and vegetable farm makes the most of winter by grooming 25 miles of trails, collecting trail fees and renting skate skis, snowshoes, fat bikes, and Nordic skis, boots and poles. Trails range from gentle beginners’ loops to rolling terrain for more advanced skiiers. Rentals are at the lodge, which has restrooms and a common room with a woodstove and room to eat your picnic lunch (hot dogs available on weekends). Hours are 9 a.m. to dusk, snow permitting. Learn-to-ski lessons are by appointment. Trail fees are $18 per adult on weekends, $15 weekdays, with discounts for children, seniors and full-time college students. For current trail conditions, call (207) 499-2678. Download the trail map at

Pineland Farms

15 Farm View Drive, New Gloucester

Pineland Farms has more than 18 miles of cross-country ski and snowshoe trails maintained with high-end grooming equipment. Cross-country ski and snowshoe equipment and fat-tire bikes are available for rent at the Outdoor Center, where trail passes are sold. Cross-country ski passes are $18 per adult, $12 after 1 p.m.; $13 for youth, $9 after 1 p.m.; and free for children 6 and under. Snowshoeing passes are $10 per person, $6 after 1 p.m. Fat tire bike trail passes are $10.


Smiling Hill Farm

781 County Road (Route 22), Westbrook

This family dairy farm just minutes from Portland maintains 15 miles of trails with varied terrain, including open field skiing, some hills and some woodlot. Skis, boots, poles and snowshoes are available for rent. Trail fees are $12 per adult, with discounts for children and teens and for access after 1 p.m. For current trail conditions and details, call (207) 775-4818.


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