Easy1.2 miWellfleet

Cannon Hill Trail

Listed & VerifiedVerified Jun 25, 2026

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What is Cannon Hill Trail like?

A short loop to the top of Cannon Hill, one of the highest points on the outer Cape, offering panoramic views of Wellfleet Harbor, Duck Harbor, and the bayside marshes. The trail passes through pitch pine and oak woodland with interpretive markers. An easy, rewarding hike for families with young children who want a big payoff for minimal effort.

Plan your walk

Cannon Hill Trail

Directions to the trailhead

Old King's Highway, Wellfleet, MA 02667

Check conditions before you go. Trail details from Cape Cod National Seashore / NPS (opens in a new tab)

When should you go?

Best time to go

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Weather and sun times from Open-Meteo for the nearest part of the Cape.

What’s the trail like?

Length: 1.2 mi
Difficulty: Easy
Surface: Natural trail
Dogs: Allowed (leashed)
Kids: Kid-friendly
Accessible: Not noted
Views: Ocean
Good for: Hiking, Walking

What should you know before you go?

Parking

Small lot off Old King's Highway near Wellfleet Center

Dogs

Allowed (leashed)

Managed by

Cape Cod National Seashore / NPS

What you'll see

Ocean views, Water views, Forest, Kid-friendly, Dog-friendly

Where is the trailhead?

Old King's Highway, Wellfleet, MA 02667.

Get directions

Get directions Open in Google Maps

Where else can you walk in Wellfleet?

Easy · 1.8 mi
Duck Creek Conservation Area Trail
Natural trail · Town of Wellfleet Conservation Commission
A peaceful loop around the tidal Duck Creek estuary near Wellfleet Center. The trail winds through red maple swamp, upland oak forest, and along tidal creek edges rich with shorebirds. A hidden gem frequented by local birders and families looking for a short, easy nature walk close to town. Connects to the cultural energy of Wellfleet Center.
CCC Visited · Verified 2026-10-05
See details
Easy · 2.14 mi
Fox Island Marsh & Whalebone Point
Natural trail · Wellfleet Conservation Trust (trails); adjoining Fox Island WMA is MassWildlife
This Wellfleet Conservation Trust trail network runs through pitch pine and oak woods between Baker Road and Pilgrim Spring Road, opening onto wide views of Fox Island Marsh and Blackfish Creek. The Trust calls the vista from Whale Bone Point the jewel of the property, and its 2.14 miles of linked trails let you make the walk as short or as long as you like. Sandy paths follow the marsh edge, where the green grass meets the tidal water. The neighboring state Fox Island Wildlife Management Area is open for hiking and wildlife viewing, and also for hunting, so wear bright colors in the fall.
CCC Visited · Verified 2026-10-06
See details
Easy
Pleasant Point Landing
Sand · Town of Wellfleet
Pleasant Point Landing is a small Town of Wellfleet landing on Blackfish Creek, at the end of a very short road off Pleasant Point Road. It's a quiet place to stand at the edge of the marsh grass and look out over the calm water, with a sandy path along the shore and boats on moorings offshore. The town directs shellfishermen here for the Blackfish Creek flats in the off-season, and the state lists it as a town launch site, which makes it handy for a kayak. Parking details weren't confirmed, so check with the town and be respectful of the neighboring homes.
CCC Visited · Verified 2026-10-06
See details
Easy · 5 mi
Wellfleet Bay Wildlife Sanctuary Trails
Mixed · Mass Audubon
Mass Audubon's flagship Outer Cape sanctuary, with about 5 miles of trails (including a 0.5-mile universally accessible loop) winding through salt marsh, pine woodland, open meadow, and barrier-beach habitats overlooking Wellfleet Harbor. Boardwalk sections cross the marsh, and the trails are a premier birding destination. A Nature Center (open 9am-5pm) anchors the property. Pets are not allowed; service animals welcome.
CCC Visited · Verified 2026-06-25
See details
Hard · 8.8 mi
Great Island Trail
Sand · Cape Cod National Seashore (NPS)
Cape Cod National Seashore's most challenging and iconic hike, threading a narrow peninsula between Wellfleet Harbor and Cape Cod Bay. Mostly soft sand with pitch-pine forest on the higher ground of Great Island and Great Beach Hill; up to about 8.8 miles round trip to the Jeremy Point overlook (a shorter ~3.9-mile loop reaches the Tavern site). Sweeping views of the Herring River, harbor, dunes, and bay. Sections flood at high tide — check tide charts. Allow 3-5 hours. Dogs are not permitted on this trail.
CCC Visited · Verified 2026-10-06
See details
Easy
Cape Cod Rail Trail (Wellfleet Section)
Paved · Massachusetts DCR
The northern end of the paved Cape Cod Rail Trail reaches South Wellfleet at LeCount Hollow Road, following the former Old Colony Railroad bed through pine and oak woodland. A flat, easy, family-friendly path for biking, walking, and jogging, connecting Wellfleet south toward Eastham and beyond. Leashed dogs welcome.
CCC Visited · Verified 2026-10-06
Where to park on the Cape Cod Rail Trail
See details

Every Wellfleet trail Trails across the Cape

Directions

What is Cannon Hill Trail like?

Where else can you walk in Wellfleet?

Easy · 1.8 mi

Duck Creek Conservation Area Trail

Natural trail · Town of Wellfleet Conservation Commission

A peaceful loop around the tidal Duck Creek estuary near Wellfleet Center. The trail winds through red maple swamp, upland oak forest, and along tidal creek edges rich with shorebirds. A hidden gem frequented by local birders and families looking for a short, easy nature walk close to town. Connects to the cultural energy of Wellfleet Center.

CCC Visited · Verified 2026-10-05

See details

Easy · 2.14 mi

Fox Island Marsh & Whalebone Point

Natural trail · Wellfleet Conservation Trust (trails); adjoining Fox Island WMA is MassWildlife

This Wellfleet Conservation Trust trail network runs through pitch pine and oak woods between Baker Road and Pilgrim Spring Road, opening onto wide views of Fox Island Marsh and Blackfish Creek. The Trust calls the vista from Whale Bone Point the jewel of the property, and its 2.14 miles of linked trails let you make the walk as short or as long as you like. Sandy paths follow the marsh edge, where the green grass meets the tidal water. The neighboring state Fox Island Wildlife Management Area is open for hiking and wildlife viewing, and also for hunting, so wear bright colors in the fall.

CCC Visited · Verified 2026-10-06

See details

Easy

Pleasant Point Landing

Sand · Town of Wellfleet

Pleasant Point Landing is a small Town of Wellfleet landing on Blackfish Creek, at the end of a very short road off Pleasant Point Road. It's a quiet place to stand at the edge of the marsh grass and look out over the calm water, with a sandy path along the shore and boats on moorings offshore. The town directs shellfishermen here for the Blackfish Creek flats in the off-season, and the state lists it as a town launch site, which makes it handy for a kayak. Parking details weren't confirmed, so check with the town and be respectful of the neighboring homes.

CCC Visited · Verified 2026-10-06

See details

Easy · 5 mi

Wellfleet Bay Wildlife Sanctuary Trails

Mixed · Mass Audubon

Mass Audubon's flagship Outer Cape sanctuary, with about 5 miles of trails (including a 0.5-mile universally accessible loop) winding through salt marsh, pine woodland, open meadow, and barrier-beach habitats overlooking Wellfleet Harbor. Boardwalk sections cross the marsh, and the trails are a premier birding destination. A Nature Center (open 9am-5pm) anchors the property. Pets are not allowed; service animals welcome.

CCC Visited · Verified 2026-06-25

See details

Hard · 8.8 mi

Great Island Trail

Sand · Cape Cod National Seashore (NPS)

Cape Cod National Seashore's most challenging and iconic hike, threading a narrow peninsula between Wellfleet Harbor and Cape Cod Bay. Mostly soft sand with pitch-pine forest on the higher ground of Great Island and Great Beach Hill; up to about 8.8 miles round trip to the Jeremy Point overlook (a shorter ~3.9-mile loop reaches the Tavern site). Sweeping views of the Herring River, harbor, dunes, and bay. Sections flood at high tide — check tide charts. Allow 3-5 hours. Dogs are not permitted on this trail.

CCC Visited · Verified 2026-10-06

See details

Easy

Cape Cod Rail Trail (Wellfleet Section)

Paved · Massachusetts DCR

The northern end of the paved Cape Cod Rail Trail reaches South Wellfleet at LeCount Hollow Road, following the former Old Colony Railroad bed through pine and oak woodland. A flat, easy, family-friendly path for biking, walking, and jogging, connecting Wellfleet south toward Eastham and beyond. Leashed dogs welcome.

CCC Visited · Verified 2026-10-06

Where to park on the Cape Cod Rail Trail

See details