45
runners
18
runs
Jogging routes around Brewster Hill offer a diverse network of trails catering to various fitness levels. The area is characterized by its extensive trail systems, including the Maybrook Trailway, which features both paved sections and paths along old train tracks. Runners can expect varied terrain, from flat routes through wetlands with wide-open skies to more challenging paths with significant elevation gains through forested areas. The landscape provides a mix of natural features, ensuring a range of experiences for joggers.
Last updated: June 28, 2026
13
runners
13.4km
01:24
80m
80m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
18
runners
9.85km
01:01
40m
40m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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9
runners
12.1km
01:15
40m
40m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
runners
5.01km
00:33
90m
90m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5
runners
4.90km
00:32
90m
90m
Easy run. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Brewster Hill
Amazing stretch of the EST! Passing the lake and along side old train tracks, wide open skies await you while passing on the trail through 'the great swamps'.
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Brewster Hill offers a diverse network of 16 jogging routes, catering to various fitness levels. You'll find options ranging from easy, leisurely runs to more challenging, difficult trails.
The terrain around Brewster Hill is quite varied. You can expect mostly paved surfaces on sections of the Maybrook Trailway, which follows old train tracks and passes through scenic wetlands with wide-open skies. Other routes, like the Haines Pond loop from Brewster, offer more varied and challenging terrain with significant elevation changes through forested areas.
Yes, there are easy options available. For a more relaxed run, consider the Running loop from Milestone Rd, which is approximately 4.9 km (3 miles) and leads through local roads and natural surroundings. This route is often completed in about 30 minutes.
For those seeking a challenge, the Haines Pond loop from Brewster is a difficult 15.1 km (9.3 miles) path known for its varied terrain and requiring good fitness. Another demanding option is the Maybrook Trailway loop from I-84 Exit 61 Park & Ride, which spans over 28 km and features notable elevation gains.
Absolutely! Many of the routes around Brewster Hill are designed as loops, offering a convenient circular experience. A popular choice is the Maybrook Trailway loop from Brewster Hill, a moderate 12.1 km (7.5 miles) route. Another option is the Running loop from MCCA, a moderate 6.7 km (4.2 miles) trail.
The routes often showcase the region's natural beauty. You'll encounter wetlands with wide-open skies, forests, and potentially scenic views of lakes or distant peaks. Specific highlights include sections of the Maybrook Trailway, and you might even catch glimpses of the Titicus Reservoir North Side. For panoramic views, consider exploring near Mount Nimham or the Ninham Mountain Fire Tower.
Yes, many trails are suitable for families, especially the easier, flatter sections. The Running loop from Milestone Rd is a good example of a shorter, less strenuous route that families can enjoy together. The mostly paved sections of the Maybrook Trailway also offer a comfortable experience for all ages.
While specific regulations can vary, many outdoor trails in the region are generally dog-friendly, often requiring dogs to be on a leash. It's always a good idea to check local signage or park regulations for the specific trail you plan to use to ensure a pleasant experience for everyone.
The komoot community frequently praises the diverse trail network and varied landscapes of Brewster Hill. With over 50 runners having explored the area using komoot, many highlight the mix of easy, paved sections and more challenging, hilly routes, as well as the scenic wetlands and forested paths that offer beautiful foliage.
While specific public transport connections directly to every trailhead may vary, Brewster Hill is accessible, and some routes, like those originating from Brewster itself, may be more conveniently reached. It's advisable to check local bus schedules or train services to Brewster for the most up-to-date information on reaching the trailheads.
Brewster Hill offers beautiful scenery year-round. In spring and summer, expect lush greenery and vibrant wetlands. Fall brings stunning foliage, making it a particularly scenic time to run. Winter runs can be beautiful, but be prepared for potentially icy or snowy conditions on trails, especially those with varied terrain. Always check local weather and trail conditions before heading out.
Many trailheads and popular starting points, especially along the Maybrook Trailway, offer designated parking areas. For example, the Maybrook Trailway loop from I-84 Exit 61 Park & Ride indicates a convenient parking option. It's generally recommended to look for specific parking information associated with your chosen route on komoot.


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