Easy1.7 miEastham

Skiff Hill Overlook & Fort Hill Loop (Hemenway Landing Spur)

Listed & VerifiedVerified Jun 25, 2026

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What is Skiff Hill Overlook & Fort Hill Loop (Hemenway Landing Spur) like?

A 1.7-mile loop beginning at the Penniman House parking lot in the Fort Hill area, connecting to Skiff Hill Overlook — one of the finest panoramic views over Nauset Marsh on the Outer Cape. A hexagonal gazebo at the summit shelters a glacial boulder with Native American sharpening grooves. The trail continues to Hemenway Landing on the marsh edge, where clammers launch and the Red Maple Swamp trail begins. A must-do for views, history, and birds.

Plan your walk

Skiff Hill Overlook & Fort Hill Loop (Hemenway Landing Spur)

Directions to the trailhead

Fort Hill Road, Eastham, MA 02642

Check conditions before you go. Trail details from NPS Cape Cod National Seashore, Eastham Chamber of Commerce (opens in a new tab)

When should you go?

Best time to go

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What’s the trail like?

Length: 1.7 mi
Difficulty: Easy
Surface: Mixed
Dogs: Allowed (leashed)
Kids: Kid-friendly
Accessible: Not noted
Views: Ocean
Good for: Hiking, Walking, Birding

What should you know before you go?

Parking

Two NPS parking lots on Fort Hill Road off Governor Prence Road; Penniman House lot and Fort Hill lot at road's end. Free.

Dogs

Allowed (leashed)

Managed by

Cape Cod National Seashore / National Park Service

What you'll see

Ocean views, Salt marsh, Water views, Bird sanctuary, Kid-friendly

Where is the trailhead?

Fort Hill Road, Eastham, MA 02642.

Get directions

Get directions Open in Google Maps

Where else can you walk in Eastham?

Easy · 1.5 mi
Salt Pond Visitor Center Trail System
Mixed · Cape Cod National Seashore / National Park Service
The gateway trail hub for Cape Cod National Seashore in Eastham. The 1.5-mile Nauset Marsh Trail skirts Salt Pond and Nauset Marsh, crossing meadows and recovering forest back to the Visitor Center. The short Buttonbush Trail (0.25 miles) is a fully accessible sensory loop with guide rope, boardwalk, and braille signs designed for visually impaired visitors. A paved 2-mile bike/walk path also connects here to Coast Guard Beach.
CCC Visited · Verified 2026-10-05
See details
Easy
Eastham Windmill (Windmill Green)
Town of Eastham
The Eastham Windmill stands on the Windmill Green in the center of town, a weathered shingled mill with its sails spread over an open lawn. The Eastham Historical Society says it was built in Plymouth about 1680, moved to Truro in the 1770s and then to Eastham in 1793, reaching its present site in 1808, and that it is the oldest and last working gristmill on the Cape. The Town of Eastham owns and maintains it, and the mill opens to visitors in July and August. Stroll the green to find the colorful Memorial Buoy Tree, built from lobster buoys, and a brick memorial plaza with the windmill rising behind it.
CCC Visited · Verified 2026-10-06
See details
Moderate · 1 mi
Fort Hill Trail
Natural trail · Cape Cod National Seashore / National Park Service
A scenic 1-mile loop over open hilltop fields above Nauset Marsh with sweeping views of the salt marsh and the Atlantic beyond. Passes the historic Captain Edward Penniman House and Indian Rock. Connects directly to the Red Maple Swamp Trail boardwalk. Hilly in places; bring insect repellent in summer.
CCC Visited · Verified 2026-06-25
See details
Easy · 1.3 mi
Nauset Marsh Trail
Natural trail · Cape Cod National Seashore / National Park Service
A 1.3-mile loop from the Salt Pond Visitor Center that traces the edge of Salt Pond and Nauset Marsh, crosses open fields, and returns through recovering forest. Excellent birding and water views; a spur connects toward Coast Guard Beach. Some sections can flood at high tide, so check conditions first.
CCC Visited · Verified 2026-06-25
See details
Easy
Wiley Park Trail (Great Pond)
Natural trail · Town of Eastham
A town conservation area on the shore of Great Pond, one of Eastham's freshwater kettle ponds. Easy walking trails wind through the Wiley conservation area with educational signs about the kettle pond, plus a small swimming beach, playground, and tennis courts. Lifeguards in summer. A relaxed, family-friendly spot away from the busier Seashore trails.
CCC Visited · Verified 2026-09-29
See details
Easy · 0.8 mi
Red Maple Swamp Trail
Boardwalk · Cape Cod National Seashore / National Park Service
A roughly 0.8-mile round-trip boardwalk that winds through the heart of a lush red maple swamp, an unusual wetland forest. Often linked with the Fort Hill Trail to form an 1.8-mile loop. Shaded and atmospheric; the elevated boardwalk keeps you above the wet ground.
Listed & Verified · Verified 2026-06-19
See details

Every Eastham trail Trails across the Cape

Directions

What is Skiff Hill Overlook & Fort Hill Loop (Hemenway Landing Spur) like?

Where else can you walk in Eastham?

Easy · 1.5 mi

Salt Pond Visitor Center Trail System

Mixed · Cape Cod National Seashore / National Park Service

The gateway trail hub for Cape Cod National Seashore in Eastham. The 1.5-mile Nauset Marsh Trail skirts Salt Pond and Nauset Marsh, crossing meadows and recovering forest back to the Visitor Center. The short Buttonbush Trail (0.25 miles) is a fully accessible sensory loop with guide rope, boardwalk, and braille signs designed for visually impaired visitors. A paved 2-mile bike/walk path also connects here to Coast Guard Beach.

CCC Visited · Verified 2026-10-05

See details

Easy

Eastham Windmill (Windmill Green)

Town of Eastham

The Eastham Windmill stands on the Windmill Green in the center of town, a weathered shingled mill with its sails spread over an open lawn. The Eastham Historical Society says it was built in Plymouth about 1680, moved to Truro in the 1770s and then to Eastham in 1793, reaching its present site in 1808, and that it is the oldest and last working gristmill on the Cape. The Town of Eastham owns and maintains it, and the mill opens to visitors in July and August. Stroll the green to find the colorful Memorial Buoy Tree, built from lobster buoys, and a brick memorial plaza with the windmill rising behind it.

CCC Visited · Verified 2026-10-06

See details

Moderate · 1 mi

Fort Hill Trail

Natural trail · Cape Cod National Seashore / National Park Service

A scenic 1-mile loop over open hilltop fields above Nauset Marsh with sweeping views of the salt marsh and the Atlantic beyond. Passes the historic Captain Edward Penniman House and Indian Rock. Connects directly to the Red Maple Swamp Trail boardwalk. Hilly in places; bring insect repellent in summer.

CCC Visited · Verified 2026-06-25

See details

Easy · 1.3 mi

Nauset Marsh Trail

Natural trail · Cape Cod National Seashore / National Park Service

A 1.3-mile loop from the Salt Pond Visitor Center that traces the edge of Salt Pond and Nauset Marsh, crosses open fields, and returns through recovering forest. Excellent birding and water views; a spur connects toward Coast Guard Beach. Some sections can flood at high tide, so check conditions first.

CCC Visited · Verified 2026-06-25

See details

Easy

Wiley Park Trail (Great Pond)

Natural trail · Town of Eastham

A town conservation area on the shore of Great Pond, one of Eastham's freshwater kettle ponds. Easy walking trails wind through the Wiley conservation area with educational signs about the kettle pond, plus a small swimming beach, playground, and tennis courts. Lifeguards in summer. A relaxed, family-friendly spot away from the busier Seashore trails.

CCC Visited · Verified 2026-09-29

See details

Easy · 0.8 mi

Red Maple Swamp Trail

Boardwalk · Cape Cod National Seashore / National Park Service

A roughly 0.8-mile round-trip boardwalk that winds through the heart of a lush red maple swamp, an unusual wetland forest. Often linked with the Fort Hill Trail to form an 1.8-mile loop. Shaded and atmospheric; the elevated boardwalk keeps you above the wet ground.

Listed & Verified · Verified 2026-06-19

See details