Attractions and Places To See around South Windham - Top 12
Best attractions and places to see around South Windham include a blend of historical sites and natural landscapes. Located within the broader Windham area, it provides access to diverse experiences. Visitors can explore historical landmarks and enjoy natural features such as rivers and trails. The region offers opportunities for outdoor activities and cultural discovery.
Best attractions and places to see around South Windham
- The most popular attractions is Jewell Falls, a waterfall that is the only natural waterfall in Portland, accessible through the Portland Trail System hiking trails. It features two main steps and small cascades, offering a natural setting within the city.
- Another must-see spot is Babb's Bridge, a bridge crossing the Presumpscot River between Gorham and Windham. This replica of an original 19th-century bridge is a notable historical site.
- Visitors also love Stroudwater Trail, a trail leading through a shady deciduous forest along the south bank of the Stroudwater River. It is part of the Portland Trails network and offers a connection to other trail systems.
- South Windham is known for its historical sites, natural trails, and river access. The area offers a variety of attractions for those interested in history and outdoor exploration.
- The attractions around South Windham are appreciated by the komoot community, with more than 7 upvotes and 7 photos shared by visitors.
Last updated: May 12, 2026
Jewell Falls
Highlight • Waterfall
newenglandwaterfalls.com/me-jewellfalls.html
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Babb's Bridge
Highlight • Bridge
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Stroudwater Trail
Highlight (Segment) • Trail
The trail soon passes under the four-lane Interstate 95, but as soon as you dive back into the forest, the roar of the road disappears. Just before reaching Spring Street, the trail leaves the river, crosses the road and changes its name to Clark Brook Trail. This trail, opening in June 2023, climbs in open terrain up to Holstein Hill on the grounds of Smiling Hill Farm.
Part of the Stroudwater Trail is closed during the winter months.
The trail is part of the Portland Trails network, a nonprofit organization in the greater Portland area.
trails.org/our-trails/stroudwater-trail
mainebyfoot.com/stroudwater-trail-portland
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Fore River Sanctuary
Highlight • Natural
The sanctuary provides important wildlife habitat, particularly in the lowland area of the Fore River, where saltwater and freshwater wetlands meet. Red oak and white pine dominate the higher elevations.
The Fore River Sanctuary is owned by Portland Trails, a Portland-area nonprofit.
trails.org/our-trails/fore-river-sanctuary
Railroad tracks from the former Portland-Lunenburg (Vermont) railway line, which is now largely closed, run through the protected area. Today, only freight traffic runs from Portland to Cumberland Mills. Interestingly, the tracks of the ‘Conway Scenic Railroad’ tourist train in the ‘White Mountains’ are part of this historic railway line.
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Stroudwater Boat Basin – Cumberland and Oxford Canal
Highlight • Historical Site
After the completion of the railroad from Boston to Portland in 1842, the canal company was no longer economically competitive and went bankrupt in 1857. The canal was closed in 1870.
The canal was added to the National Register of Historic Places in 1974.
mrlakefront.net/newsdetails.taf?date=01/21/2009&link=cumberland--oxford-canal-played-big-role-in-regions-history- en.wikipedia.org/wiki/Cumberland_and_Oxford_Canal
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Tips from the Community
I love this bridge. But, a dump truck tried to cross it and collapsed the floor. Not sure the repair time frame. 9/21/24
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The 'Jewel Falls' is a natural waterfall in Portland's 'Fore River Sanctuary'. The waterfall is located on the 'Portland Trails' network in the nature reserve. At the end of May 2024, the water will only flow as a trickle over the rocks down into the wetland. https://www.newenglandwaterfalls.com/me-jewellfalls.html
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The Cumberland and Oxford Canal was built between 1827 and 1892 to connect Long Lake and Sebago Lake with the seaport of Portland in southeastern Maine and to transport mainly lumber and agricultural products by boat. The canal followed the Presumpscot River from Sebago Lake and branched off the river at Westbrook to the Fore River and the port of Portland. The navigable distance was about 61 km from Harrison at the northern end of Long Lake to Portland. Horses on the shore path pulled the boats along the canal. After the completion of the railroad from Boston to Portland in 1842, the canal company was no longer economically competitive and went bankrupt in 1857. The canal was closed in 1870. The canal was added to the National Register of Historic Places in 1974. https://www.mrlakefront.net/newsdetails.taf?date=01/21/2009&link=cumberland--oxford-canal-played-big-role-in-regions-history- https://en.wikipedia.org/wiki/Cumberland_and_Oxford_Canal
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The Fore River Sanctuary is an 85-acre nature reserve that includes Jewell Falls, a natural waterfall and site of the historic Cumberland and Oxford Canal. Small parking lots are located at the Stroudwater Trailhead and the Jewel Falls Rowe Trailhead. Parking is also available at the Southern Maine Pediatric Dentistry parking lot, but only in the five marked spaces near Frost Street. The sanctuary provides important wildlife habitat, particularly in the lowland area of the Fore River, where saltwater and freshwater wetlands meet. Red oak and white pine dominate the higher elevations. The Fore River Sanctuary is owned by Portland Trails, a Portland-area nonprofit. https://www.trails.org/our-trails/fore-river-sanctuary/ Railroad tracks from the former Portland-Lunenburg (Vermont) railway line, which is now largely closed, run through the protected area. Today, only freight traffic runs from Portland to Cumberland Mills. Interestingly, the tracks of the ‘Conway Scenic Railroad’ tourist train in the ‘White Mountains’ are part of this historic railway line.
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The Stroudwater Trail begins at a small (free) parking lot on Congress Street, just after the road crosses the Stroudwater River. The trail leads through a shady deciduous forest along the south bank of the river. In the dry season, the numerous streams that flow into the river carry little water. Along the way, a sign reminds you that a pedestrian bridge is to be built over the Stroudwater River here to connect the trail to the Fore River Sanctuary trail network. The trail soon passes under the four-lane Interstate 95, but as soon as you dive back into the forest, the roar of the road disappears. Just before reaching Spring Street, the trail leaves the river, crosses the road and changes its name to Clark Brook Trail. This trail, opening in June 2023, climbs in open terrain up to Holstein Hill on the grounds of Smiling Hill Farm. Part of the Stroudwater Trail is closed during the winter months. The trail is part of the Portland Trails network, a nonprofit organization in the greater Portland area. https://www.trails.org/our-trails/stroudwater-trail/ https://mainebyfoot.com/stroudwater-trail-portland/
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The picturesque Jewell Falls, with its two main steps and small cascades, are the only natural waterfalls in Portland. They are accessible through the Portland Trail System trails, and you'll quickly forget that you're in the city.
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A really beautiful idyllic place. But you shouldn't go at low tide. The waterfall is definitely more impressive at high tide.
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Babb's Bridge is a covered bridge that crosses Presumpscot River between the towns of Gorham and Windham. The current bridge is a replica of the original bridge that was built in the 19th century and was destroyed by arson in 1973.
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Frequently Asked Questions
What natural attractions can I explore around South Windham?
South Windham offers several natural attractions. You can visit Jewell Falls, the only natural waterfall in Portland, accessible via the Portland Trail System. The Fore River Sanctuary, an 85-acre nature reserve, also encompasses Jewell Falls and provides important wildlife habitat. Further afield, you can enjoy Sebago Lake and Little Sebago Lake for boating and swimming, or explore Dundee Park with its beach along the Presumpscot River.
Are there historical sites to visit in South Windham?
Yes, South Windham and the broader Windham area are rich in history. The Gambo Gunpowder Mill is a significant Civil War-era site. You can also find historic homes on Main Street, the Guilford Smith Memorial Library, and the South Windham Library & Railroad Museum. The Old Grocery at Windham Center houses the Windham Historical Society museum, offering insights into the region's past. Additionally, the Stroudwater Boat Basin – Cumberland and Oxford Canal marks a historical transportation route.
What trails are available for walking or hiking near South Windham?
For walking and hiking, the Stroudwater Trail offers a shaded path along the Stroudwater River, connecting to other trail systems. The Fore River Sanctuary also features trails, including access to Jewell Falls. Other options include Donnabeth Lippman Park with a looping trail around a pond, and the extensive Lowell Preserve and East Windham Conservation Area, offering over 8 miles of trails for various activities.
Are there family-friendly attractions or activities in the area?
Many attractions around South Windham are family-friendly. Jewell Falls and the Fore River Sanctuary are great for nature walks. Donnabeth Lippman Park features a Storybook Trail for young hikers. Dundee Park offers a beach, picnic area, and sports courts. The historical Babb's Bridge is also a notable spot for families to visit.
Where can I go cycling around South Windham?
South Windham offers several cycling opportunities. You can explore routes like the Moody Trail System loop or the Mountain Division Trail to River Road loop. A moderate option is the Middle Jam Road & River Road loop via Babb's Bridge. For more options, check out the Cycling around South Windham guide.
What are some running trails near South Windham?
Runners can find various trails, including the Cherry Hills Trail loop in Westbrook or the Sebago Lake Land Reserve loop via Half Moon Trail. For a longer, more challenging run, consider the Poplar Ridge – Lowell Preserve loop. Discover more running options in the Running Trails around South Windham guide.
Are there mountain biking trails in the South Windham area?
Yes, mountain biking enthusiasts can explore trails such as the Weeks and Moody Trail Systems loop or the Lowell Preserve and Blackstrap Hills Loop. The Moody Trail System also offers several loops from different starting points. For a comprehensive list, refer to the MTB Trails around South Windham guide.
What is the significance of Babb's Bridge?
Babb's Bridge is a historic covered bridge that spans the Presumpscot River between Gorham and Windham. The current structure is a replica of the original 19th-century bridge, which was unfortunately destroyed by arson in 1973. It stands as a notable historical landmark in the area.
Can I find viewpoints or scenic spots in South Windham?
While not explicitly designated viewpoints, natural attractions like Jewell Falls offer picturesque settings. The Lowell Preserve and East Windham Conservation Area also provide scenic vistas, with some points even offering views of the White Mountains.
What is the Cumberland and Oxford Canal?
The Cumberland and Oxford Canal was a significant historical waterway built between 1827 and 1892. It connected Long Lake and Sebago Lake with the seaport of Portland, primarily for transporting lumber and agricultural products. Today, the Stroudwater Boat Basin – Cumberland and Oxford Canal is a historical site marking a section of this important canal.
Are there any parks with recreational facilities?
Dundee Park is a community resource featuring an attractive beach and picnic area along the Presumpscot River. It offers opportunities for swimming, basketball, and volleyball. Donnabeth Lippman Park, formerly Chaffin Pond, is another 123-acre park with woodlands, wetlands, and a looping trail, ideal for hiking and snowshoeing, with fishing and non-motorized boating permitted.
What is the Windham Historical Society's role in the area?
The Windham Historical Society actively works to raise public awareness of historic places throughout Windham, including South Windham. They operate a museum at the Old Grocery at Windham Center, preserving and showcasing the region's rich history. You can learn more about their projects and activities on their website: windhamhistorical.org.
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