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!

In Their Footsteps: Cape Cod History - Cape Cod's Woodstock

The original Woodstock music festival is widely considered to be one of the most important moments in the history of music. From August 15-18, 1969 an estimated 400,000 people crowded onto Max Yasgur’s farm in Bethel, New York. The list of musical acts that played during the festival reads like a who’s who of icons. Legends like Jimi Hendrix, Grateful Dead, Janis Joplin, Crosby, Stills, Nash, and Young, The Who, and more graced the stage enthralling the crowd. 

Two years later in August 1971 former Beatle George Harrison and Indian sitarist Ravi Shankar organized the Concert for Bangladesh. Taking place in New York City’s Madison Square Garden it was a pair of benefit shows to raise money and awareness for the refugees of East Pakistan, following the Bangladesh Liberation War-related genocide. The shows were attended by 40,000 people and by 1985 the concerts and subsequent investments had raised nearly $12 million. 

One year later in May 1972 those first two events collided in the dunes of Provincetown on Cape Cod. An idea was hatched for a Woodstock-type concert benefiting Bangladesh. Who organized it? Who played it? Was it a success? This is the story of Cape Cod’s Woodstock. 

The roots of this event began in December 1965 with the creation of the Provincetown Academy of Living Arts. This was a nonprofit year-round arts center where students and professional artists alike could study and perform. However after two years the organization was still looking for a physical home base for operations. In 1969 they expanded their operations and began holding and sponsoring art festivals. Things came together when 20-year old Harwich resident David Blackmore pitched the idea of the day long outdoors music and arts festival to the organization in early 1972. It was to be a free event hopefully with donations from attendees going to support Bangladesh. Although there was minor resistance from locals the Cape Cod National Seashore granted the festival. Dubbed the Provincetown Music and Arts Festival it was promoted throughout New England by Blackmore, something beyond what the National Seashore had anticipated. Despite that fact Blackmore expected only between 1,000-1,500 people to show up. 

The location chosen for the event was the Province Lands Amphitheater, which could seat 700, with a date of Sunday May 28, 1972. It was scheduled during one of the busiest weekends of the year, Memorial Day Weekend. It was a nearly-perfect weekend weather-wise. Not only was the event given the green light by the Cape Cod National Seashore, a section of dunes on Race Point Beach was opened up to allow concert goers who could not find accommodations a place to sleep. People, cars, motorcycles, and more lined the dunes and the streets of Provincetown. It was a far larger crowd than Blackmore had anticipated filled with hippies, Hells Angels, and more. Rumors would permeate the crowd in the time leading up to the show of potential big name acts at the event all the way up to a Beatles reunion. None of those rumors came to pass though. 

The Province Lands Amphitheater

(Christopher Setterlund)

The show began at 10am on Sunday and was packed with bands from the Cape and Boston. The top performer as far as Cape Codders go was Marie Marcus, the Cape’s First Lady of Jazz. However the top performer for connections to present-day was The Daddy Warbucks Band. At the time they had toured with Rod Stewart. Two of the members of the band were Marshall Bruce Mathers and his wife Debbie, their son, born only a few months after the show, went on to become iconic rapper Eminem. The other acts on the bill were: Albatross, who played in Falmouth; Flight, a brass band from Springfield; Keith Troupe, a newly formed band in the Harwich-Chatham area; L Z Band, a blue and jazz band from Boston; and Sadbird, recently of the Groggery in Boston. 

Thousands in attendance at the festival.
(Cape Cod National Seashore Archives)

All in all somewhere between 8-12,000 people crowded in and around the Race Point Amphitheater to hear the live music and show their support. Unfortunately the large, lively crowd for the event did not translate to large donations for Bangladesh. Before the festival was over it was announced that a mere $100 had been collected from those in attendance, or roughly $1 for every 120 people. It did not stop there as in the aftermath of the show it was revealed by Provincetown Police Chief James Meades that the festival may have been more harm than good. 

Crowds of people around the Province Lands Visitors Center
(Cape Cod National Seashore Archives)

The large number of people on the dunes caused extensive damage. The night before many had torn up beach fencing and shingles from National Seashore buildings to burn for warmth. Drug and alcohol use ran rampant before and during the event and at one point part of the Province Lands Visitors Center’s roof was set on fire. The end result was Meades proclaiming he would go to Federal court to file and injunction if another similar festival was ever planned. In spite of all that then-Superintendent of the Cape Cod National Seashore Leslie Arnberger applauded the efforts of the Park Rangers and the members of the U.S. Park Police that had been dispatched from Washington D.C. for keeping the enormous festival relatively contained. 

It was a moment in history of Cape Cod and the youth of the early 1970’s. It was an event not likely to ever be duplicated, or even allowed, on the Cape again. For one day in May 1972 Woodstock, Bangladesh, and Cape Cod culture all converged in the dunes of Provincetown. 

My 5th book, Cape Cod Nights, is on sale at Amazon.com and through Arcadia Publishing

View my previous blog posts: In Their Footsteps: Cape Cod History - The Wreck of the Montclair

In My Footsteps: Hudson, New York

                              

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