New Trail on Big Tip Toe

Bench and Trail Added

VLT steward Kerry Hardy likes to go out on one of the hottest days of summer and make new trails...AND carry a new bench up this new trail. Above is a map showing the newer, easier, less steep trail to the same lovely view with a new bench to rest and enjoy the beauty of the Fox Island Thorofare.



Tip Toe Mountain Preserve

Size: 40 acres

Be Aware:

  • Foot traffic only. Please do not hike on the right-of-way to the private residence (see map).
  • Please stay on trails, especially at the summits. These all have near-vertical drop-offs, so please watch children closely.
  • The existing traditional access to Big Tip Toe is a short, steep scramble up over bare ledges. This is very challenging terrain, especially when wet. Please use good judgement and caution when attempting this. There is a newer, more gradual climb to the same lovely view with a bench to rest and enjoy the view of the beauty of the Fox Island Thorofare.
  • The stone dam crossing on the shore trail is submerged for roughly an hour on either side of high tide; hikers should consult the tide charts posted on the trail to avoid getting stranded.

Features: Multiple panoramic views of islands and ocean, from the northwest all the way around to the east, interesting bedrock geology; walkable shoreline; and very high biodiversity in a small area.  

Directions: Turn left from the ferry terminal, go 0.4 miles, then right on Old Harbor Rd for 0.3 miles. Bear left onto North Haven Road for 6.4 miles to where Tip Toe Mountain Road (gravel) will be a left turn. Drive 1.2 miles, the gravel parking lot will be on your left. A nearby kiosk marks the Middle Tip Toe Loop trailhead. 


  • Middle Tip Toe Loop – .5 miles, mostly shady and with easy grades for all hiking abilities. 
  • Shore Trail – On the right is the entrance to a longer trail down to the shore, with an additional loop should the trail over the colonial era stone dam be inaccessible at or near high tide. Check the tide chart posted at the trailhead to help plan your hike.
  • New Trail on Big Tip Toe – This is a short, steep climb from the head of the gorge, a longer trail to the same view has been added, more gradual, less steep.