Hiking Cape Cod 2025 - In My Footsteps

With summer comes the increased desire to get out and enjoy the beautiful weather. Living on Cape Cod, there is no shortage of places to see and explore. Hiking is a fantastic way to get out into nature, get some exercise, and explore the great outdoors. However, hiking can also be dangerous if you're not prepared or don't take the necessary precautions.

What I am going to do here is share some amazing places to explore on Cape Cod and also provide some tips on how to enjoy hiking outdoors safely.




1. Plan your route: Before you start your hike, it's essential to plan your route. Luckily, Cape Cod is a peninsula, and the odds of getting lost somewhere truly inhospitable are small. However, it is important to have a general sense of where you are and where you are going. Doing a little research won’t hurt. Select a trail that suits your fitness level and experience. For the most part, Cape Cod is a series of beginner to moderate hiking trails.

2. Bring the right gear: This is a given. Make sure you have appropriate footwear that provides good support and traction. Wear comfortable clothing that is appropriate for the weather conditions. If the hike is long enough, bring a backpack with essential items such as water, snacks, sunscreen, a hat, and maybe a first aid kit. There are plenty of short hikes on Cape Cod, but there are also some that can be up to ten miles or longer.

3. Check the weather forecast: This is true for any time of year. Hiking is fun, but hiking in the pouring rain, wind, or snow is not. That’s not to say that some inclement weather can’t make for a fun adventure. The main point is to think ahead. A little drizzle or hot temperatures might not ruin a hike, but a downpour can change the complexion of a trail, turning packed dirt to slippery muck.

4. Hike with a buddy: It's always a good idea to hike with a buddy or a group of people. Not only is it more fun to hike with others, but it's also safer. If you get lost or injured, you'll have someone there to help you.

5. Stay on the trail: When hiking, always stay on the trail. Don't wander off the path, as you can damage the environment and get lost. There is also a prevalence of ticks that can cause Lyme Disease. Most trails are crafted to make sure you get the best experience, so diverting from them shouldn’t be necessary.

6. Pace yourself: Hiking can be physically demanding. Don't push yourself too hard and listen to your body. If you feel tired or lightheaded, take a break and have a snack or drink some water. It also gives you ample time to take in the scenery and even snag a couple of amazing photos.

7. Respect wildlife: Remember when hiking, you’re in nature’s house. Keep your distance from animals and don't disturb their natural habitat. Don't feed animals or leave food out, as this can attract wildlife and create dangerous situations.

8. Leave no trace: This is most important. Leave no trace behind, and avoid damaging the environment by carving your name into trees or rocks. Take out what you take in. We only have one environment, and it is important to leave its beauty for future generations.



That’s a pretty comprehensive list, but it’s all common-sense stuff. Be smart, be respectful, and be prepared. Now that you know how to properly enjoy a good hike on Cape Cod, it’s time to share a few places to implement the tips. They will also be designated as easy, moderate, or difficult so that all experience levels can find somewhere incredible to visit.


Great Island Trail: Wellfleet – Moderate: This trail can be easy or moderate, depending on the path you take. It is anywhere from 3.9 – 8.8 miles in total length. There are spectacular views of Cape Cod Bay and Jeremy Point. The uplands take you past the 17th-century Samuel Smith Tavern Site.


Wing Island Trail: Rt. 6A, Brewster – Easy: It is important to check the tide before you go, as it is possible for the water to come in and make Wind Island, well, an island. The trail is roughly 1.5 miles in total. It leads to spectacular views of Cape Cod Bay and the famed Brewster Flats.


Dead Neck Trail: Mashpee – Easy: This trail extends west from the parking lot of South Cape Beach. It is mostly over sand, so it can be more challenging in different areas. In total, it is about 2.5 miles out and back. The end of the trail brings you to the mouth of Waquoit Bay, which can be a highway for boats in the summer and feel like the middle of nowhere in the winter.


West Barnstable Conservation Loop: Crooked Cartway, West Barnstable – Moderate: This is a long and somewhat hilly trail extending as much as nearly 7 miles if you do the entirety of it. The challenge of the hills is well worth it for the spectacular view from the Walker Point Deck, one of the highest locations on Cape Cod.


Province Lands Bike Trail: Province Lands Rd, Provincetown – Easy/Moderate: Despite being a paved trail, this 6.7-mile loop traverses up and down the rolling sand dunes of Provincetown. The views are incredible, and there are several parking areas along the trail. This means that you can choose to hike a shorter distance if desired.


Harding’s Beach Trail: Harding’s Beach Rd., Chatham – Moderate: Although it only clocks in at about 2 miles, this trail is moderately challenging due to it being mostly over soft sand. To the north, you’ll see Oyster Pond River, to the south the ocean, and in front of you, Stage Harbor Lighthouse. It feels like the middle of nowhere, even as the boats pass by in and out and Stage Harbor.

Of course, there are hundreds of other incredible trails to be explored on Cape Cod. These are only a few examples. Wherever you choose to walk, be sure to be safe and have fun. Enjoy the rest of summer!

Cape Cod Nauset Beach Winter Storm Riley Livestream 2018 - Found Footage After 8 Years!

March 4, 2018, Winter Storm Riley tore through Cape Cod with winds gusting over 90 mph. Even worse was the storm surge and erosion. I went live on Facebook on location at Nauset Beach in Orleans during the storm's peak. My phone's battery died during the stream, and I could not find the footage on Facebook. Since I never officially 'ended' the stream, I figured it was not saved and, therefore, lost. I looked many times over the years with no luck. Then this week by happenstance I was looking for a different post when lo and behold I found the raw footage in my archives. What we have here is that livestream footage of Winter Storm Riley at its peak forever changing one of Cape Cod's most iconic locations. I did my best to remaster the video, fix the audio due to the intense winds, and even add captions where I could to make the viewing experience as good as it could be. To listen to episodes of the In My Footsteps Podcast click here: https://inmyfootstepspodcast.buzzsprout.com/ Become A Subscriber to the Podcast on Patreon: patreon.com/InMyFootstepsPodcast

Hurricane Lee, Cape Cod, MA 4K

In My Footsteps: Trip 12: Orleans, Mass.

In My Footsteps

Christopher Setterlund

Trip 12: Orleans, Mass.

January 26, 2010

From the air Cape Cod is shaped like an arm with the Cape Cod Canal at the shoulder and Provincetown as the hand.  If we see Cape Cod in that way then Orleans would be considered the elbow, and in many ways it is.  The elbow connects the upper and lower arm, Orleans connects the two segments of Cape Cod as well.  West of Orleans is the more modern segment of the Cape including larger towns like Hyannis and Falmouth.  East and North of Orleans house the quainter and more secluded spots on the Cape like the National Seashore.  Orleans represents the last real taste of 21^st Century Cape Cod on the way to the Outer Cape. 

A trip to Orleans, especially in summer, inevitably leads you to the famous Nauset Beach(right).  Nauset Beach, named for the Native American tribe that originally inhabited the area, is one of the best spots to surf up and down the east coast and is one of the most popular as well.  Being located along where Nantucket Sound and the Atlantic Ocean collide, Nauset Beach is privy to some rough seas and large waves.  Even on a day like today, when the tide was low, the waves were larger than anything seen along the shores of Cape Cod.  Even if you are not a surfer, or even if you don’t like to swim, taking a walk along Nauset Beach is a must.  Listening to and watching the waves crash on the shore is a soothing almost meditative experience, if you lose yourself in the moment you may look up and suddenly find yourself miles from the parking lot!

The road to Nauset Beach itself holds some great places to eat like the Nauset Beach Club Restaurant, but there are some neat sights as well.  One such place is the little known, out of the way Sea Call Farm(left).  Located off of Nauset Beach Road on Tonset Road, this historic site was actively farmed from 1931-1950 and is now a conservation area owned by the town.  It can be walked year round and a pathway behind the farmhouse leads to a breathtaking view across Town Cove to a state boat ramp near the Orleans Rotary. 

As you head away from the Atlantic Ocean side of Orleans toward the Cape Cod Bay side you pass another historic site along Rt. 28 that can be very easy to miss.  Windmills, like lighthouses, are synonymous with Olde Cape Cod.  As if symbolizing Orleans’s status as the separation between the old and new of Cape Cod the Jonathan Young Windmill(left) sits directly across from the last major shopping center as you travel east along the Cape.  The Jonathan Young windmill was originally built 1720 in South Orleans and in 1897 was actually moved to Hyannisport.  In 1983 the windmill was given to the Orleans Historical Society in 1983 and subsequently donated to the town.  It is open to the public in July and August.  The windmill park is located right on Town Cove which is easy to walk down to from the site.

Located on the other side of Orleans are two more spots that must be seen and enjoyed on any trip to the Cape.  Skaket Beach and Rock Harbor both face Cape Cod Bay and are filled with amazing scenery.  Skaket Beach lies at the end of Skaket Beach Road while Rock Harbor is easy to find from either Rt. 6A or the Orleans Rotary.  You may walk Skaket Beach all the way to the Namskaket Marsh located a little over half a mile away. 

Rock Harbor and Skaket Beach(right) are both places to go for splendid sunsets.  At Rock Harbor there are trees spaced out into the harbor that help to guide boats.  It is a sight that will make you do a double take when it is first seen and what Rock Harbor is known for.  The trees are not there during the winter time and I am not sure what is done with them.  There is plenty of parking, the beach on the western side of the harbor can be walked to a salt marsh while the eastern side of the harbor walk can be taken to Boat Meadow.

While it may be a sort of gateway between old and new on Cape Cod, Orleans has more than its share of places to see.  Make sure to stop in and see these places on your way to wherever you are going.  Have fun and happy traveling!

Directions: Nauset Beach: From Rt. 28 East, turn right onto Main Street.  There are signs leading to Nauset Beach.  Follow Main Street, it becomes Beach Road.  Follow this road to the beach parking lot.

Sea Call Farm: From Rt. 28 East, turn right onto Tonset Road.  Follow it for just over half a mile.  Sea Call Farm appears on the left side.

Jonathan Young Windmill Park: Take Rt. 28 East until it intersects with Rt. 6A.  The windmill park is 1,000 feet ahead on the right side.

Rock Harbor: From Orleans Rotary take exit marked Rock Harbor Rd.  Follow this road for 1.5 miles until you reach the harbor.  The main parking area is on the left side.

Skaket Beach: From Rt. 28 East turn left on Eldredge Pkwy.  Continue onto W Rd. and subsequently onto Skaket Beach Rd.  Follow this to the parking area.

References: Orleans Historical Society

Orleans on Dwellable

In My Footsteps: Trip 11 - Eastham, Mass.

In My Footsteps

Christopher Setterlund

Trip 11: Eastham, Mass.

January 26, 2010



It is the gateway to the Outer Cape. Once you pass through the Orleans Rotary into Eastham it is as if you have traveled to a different place and time. Except for very sparse clusters of shops and restaurants along Route 6 the remainder of Cape Cod up to Race Point in Provincetown is nearly unchanged from the 19th Century. It is out here that the true soul of Cape Cod can still be felt. Eastham is only the first stop through the Outer Cape, but like the other towns it has many amazing sights that need to be discovered.

The first place comes up on you fast along Route 6. A sign on the right points you toward Fort Hill. Before reaching the scenic overlook there is a parking lot on the left directly across from a piece of Cape history. The Penniman House(left), built in 1867 by rich whaler Captain Edward Penniman, was the most expensive house in town when it was built. It was a testament to his fortune he had gained through seven successful whaling voyages; his love for whaling is also depicted by the pair of whale ribs acting as a trellis to enter the front yard. After taking a stroll around the grounds of this marvelous olde mansion it is a short drive up to the lookout area of Fort Hill. There is a panoramic view of Salt Pond Bay and the Atlantic Ocean with a trail to lead you down to the water, or back toward the Red Maple Swamp.

The next stop up along Rt. 6 is First Encounter Beach(right). A left turn at the set of lights at Samoset Road leads you past Windmill Green. This winding road will take you to the beach area. This beach is historic as it is the place where the initial, peaceful meeting between Myles Standish and the crew of the Mayflower met up with the local Nauset Indians in 1620. The Mayflower crew kept on to Plymouth and the village of Eastham was not settled by the Pilgrims for another twenty-four years in 1644. At low tide there is a mass of open wet sand and mudflats for shell fishing. There are frequent seal and sea turtle sightings along the eastern most Cape beaches and signs posted around them alert you to this fact and ask you to leave them alone.

Nauset Road, a right turn less than a mile from Samoset Road takes you to my favorite spot in the town of Eastham: Nauset Light(right). Nauset Light, located on a hill overlooking the similarly named Nauset Light Beach, was originally built in Chatham in 1877. The cast iron giant was to be dismantled in 1993 but was saved through a tremendous effort by the Nauset Light Preservation Society. It is open Sunday’s during the spring, summer, and fall.

There are actually three more lighthouses located only a third of a mile away on Cable Road. The ‘Three Sisters’ lighthouses can easily be missed by travelers as they are not located on the shores of Cape Cod, but instead they sit spaced out across an open field. Their story is possibly the most amazing of all of the Cape lighthouses but it also the least known.

The diminutive Three Sisters, only fifteen feet tall as opposed to the forty-eight foot tall Nauset Light, originally sat overlooking Nauset Light Beach from as far back as 1838. The original brick houses were replaced in 1892 with the wooden structures that are still standing. After being systematically separated during the 1920’s to make way for the recently moved Nauset Light, the Three Sisters were one by one purchased by the National Park Service. In 1983, after 73 years apart the Sisters were reunited in the field where they currently sit. They were restored and placed in the field at the same distance apart as they had been when they watched over the Atlantic. Only the middle Sister(left), the last one that stood over Nauset Light Beach, still has its lantern adorning its top; there was not enough funding to repair the lantern rooms on the other two.

Nauset Light Beach, as well as most beaches up and down the National Seashore area of Cape Cod, showcase the biggest waves and are hot spots for surfers at all time of year. During this trip there were several surfers out on the waters near Coast Guard Beach located at the other end of Ocean View Drive from Nauset Light. The Outer Cape in general due to the rough seas has claimed more than 3,000 vessels in 400 years. It was this fact that led to the founding of the Massachusetts Humane Society which set up nine stations along the eastern coast of Cape Cod. They would be there to rescue and assist any ships in need. There is a set of trails that lead from Coast Guard Beach to Nauset Marsh. The boardwalk area is great for bird watching and photography.

Though it is considered the gateway to the National Seashore by many, Eastham is a prime spot for nature and history. Rather than just passing through on your way to the Seashore or to Provincetown make it a point to check out the places mentioned here as well as many of the other gems hidden around this 350-year old village. Have fun and happy traveling!

Directions: Fort Hill & Penniman House: Follow Rt. 6 north, there is a sign for Fort Hill. Bear right, the Penniman House is on the right, the Fort Hill overlook is straight ahead.

First Encounter Beach: Follow Rt. 6 north for just over 2 miles after Orleans Rotary. Turn right at sign for First Encounter Beach at Samoset Rd. Follow the road to the beach.

Nauset Light: Follow Rt. 6 north 2.75 miles, bear right onto Nauset Rd. Keep straight, road turns into Doane Rd., turn left onto Ocean View Rd. Follow it to the end. Nauset Light should be visible, Nauset Light Beach parking lot is on the right. The Three Sisters Lighthouses are a 1/3mi. walk down Cable Rd.

Coast Guard Beach: From Nauset Light Beach follow Ocean View Dr. back south.

References: Cape Cod Travel - Eastham

The Three Sisters Lighthouses

Nauset Light Preservation Society

Eastham on Dwellable