AMBLEWAY Wildest hikes

Sunset hikes near Winchester Highlands, ma

A short walk out, the whole show, and back at your car before dark. Times are estimates at a relaxed pace; give yourself extra buffer, especially with kids or in a group.

3 of 12 spots
  1. Horn Pond Mountain–Nolan's Viewpoint, 4 beaches 2.1 mi away

    Leave by 6:22 PM

    1. Leave trailhead6:22 PM
    2. Sunset6:47 PM
    3. Head back7:02 PM
    4. At your car7:06 PM
    5. Dark7:16 PM

    Back at your car by 7:06 PM — 9 min before dark.

    0.2 mi to the viewpoint · 9 min of walking

  2. Horn Pond & Horn Pond Conservation Area Beach 2 mi away

    Leave by 6:26 PM

    1. Leave trailhead6:26 PM
    2. Sunset6:47 PM
    3. Head back7:02 PM
    4. At your car7:04 PM
    5. Dark7:16 PM

    Back at your car by 7:04 PM — 12 min before dark.

    0.1 mi to the viewpoint · 3 min of walkingCar visible from the viewpoint

  3. Tri-Community Greenway 0.9 mi away

    Leave by 6:26 PM

    1. Leave trailhead6:26 PM
    2. Sunset6:47 PM
    3. Head back7:02 PM
    4. At your car7:04 PM
    5. Dark7:15 PM

    Back at your car by 7:04 PM — 12 min before dark.

    0.1 mi to the viewpoint · 4 min of walking

  4. rock sofa–North Reservoir, 4 lakes 0.4 mi away

    Be there by 6:27 PM

    1. Be there6:27 PM
    2. Sunset6:47 PM
    3. Dark7:15 PM

    Your car is right there — dark at 7:15 PM.

    The viewpoint is right at the trailhead

  5. Winthrop Hill–Taylor Mountain, 6 lakes 0.5 mi away

    Be there by 6:27 PM

    1. Be there6:27 PM
    2. Sunset6:47 PM
    3. Dark7:15 PM

    Your car is right there — dark at 7:15 PM.

    The viewpoint is right at the trailhead

  6. South Reservoir–Bellevue Pond, 4 lakes 1.4 mi away

    Be there by 6:27 PM

    1. Be there6:27 PM
    2. Sunset6:47 PM
    3. Dark7:15 PM

    Your car is right there — dark at 7:15 PM.

    The viewpoint is right at the trailhead

  7. Long Pond & Cranberry Pond Path via Nanepashemet Road 0.8 mi away

    Be there by 6:27 PM

    1. Be there6:27 PM
    2. Sunset6:47 PM
    3. Dark7:15 PM

    Your car is right there — dark at 7:15 PM.

    The viewpoint is right at the trailhead

  8. Middlesex Fells Reservation Viewpoint & Long Pond via Nanepashemet Road 0.8 mi away

    Be there by 6:27 PM

    1. Be there6:27 PM
    2. Sunset6:47 PM
    3. Dark7:15 PM

    Your car is right there — dark at 7:15 PM.

    The viewpoint is right at the trailhead

  9. Pipeline Trail & Whispering Hill Loop 4.1 mi away

    Leave by 6:15 PM

    1. Leave trailhead6:15 PM
    2. Sunset6:48 PM
    3. Head back7:03 PM
    4. At your car7:10 PM
    5. Dark7:16 PM

    Back at your car by 7:10 PM — 5 min before dark.

    0.3 mi to the viewpoint · 140 ft climb · 20 min of walking

  10. Mill Pond Reservoir Loop via Bridge and Cliff 4.4 mi away

    Leave by 6:17 PM

    1. Leave trailhead6:17 PM
    2. Sunset6:48 PM
    3. Head back7:03 PM
    4. At your car7:13 PM
    5. Dark7:16 PM

    Back at your car by 7:13 PM — 3 min before dark.

    0.4 mi to the viewpoint · 20 min of walking

  11. Whispering Hill–Babylon Hill, 5 sights 4.4 mi away

    Leave by 6:17 PM

    1. Leave trailhead6:17 PM
    2. Sunset6:48 PM
    3. Head back7:03 PM
    4. At your car7:11 PM
    5. Dark7:16 PM

    Back at your car by 7:11 PM — 4 min before dark.

    0.4 mi to the viewpoint · 60 ft climb · 20 min of walking

  12. Mudhole Pond–Ali-Waji, 3 sights 6.9 mi away

    Leave by 5:45 PM

    1. Leave trailhead5:45 PM
    2. Sunset6:48 PM
    3. Head back7:03 PM
    4. At your car7:44 PM
    5. Dark7:16 PM

    Back at your car by 7:44 PM, after dark — bring a headlamp.

    1.5 mi to the viewpoint · 180 ft climb · 85 min of walking

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