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Nantucket is known for its gorgeous beaches, lighthouses, hundreds of historic buildings, and stunning nature. Best of all, the island is so tiny and has so many walking trails, paths, and places for leisurely strolls, that you can easily explore its beauty and most of its scenic views on foot.

Located just 30 miles south of the coast of Cape Cod, Massachusetts, this paradise-like island offers endless opportunities for outdoor lovers and adventurers.

Since getting your car to Nantucket is expensive, and parking can be a problem, especially during the peak of the summer, it is recommended to leave your vehicle behind when visiting it.

You can rent a bike or car there, or you can use the regular buses or local cabs to get around.

But undoubtedly, the best way to experience the vibes and charm of Nantucket is by walking, hiking, or cycling.

Plus, you can find suitable accommodation for your Nantucket escape in just about every neighborhood and area of the island, depending on your plans.

Here are some of the best walks to enjoy during your trip to the “Little Grey Lady of the Sea.”

Sconset Bluff Walk

Also known as Cliff Walk, this walking path is one of the top instagrammable and favorite walkways on the island.

The mile-long path passes through the village of Siasconset and will allow you to admire the famous shingle-style cottages with crawling roses reaching the rooftops and beautiful blossoming gardens from as close as possible.

The peaceful shell-covered path reaches the dramatic cliffs on the east coast of Nantucket, or you can take a turn and head off to the vast and beautiful Siasconset Beach and the iconic Sankaty Head Lighthouse.

Tupancy Links

This lovely area is located a mile from Main Street Downtown and is among the most popular spots for walking, hiking, picnics, dog walking, and bird watching.

The parcel is 73 acres in size and has 1.5 miles of easy trails that will take you by what used to be the holes, tees, and greens of this former golf course. The walking path also offers mesmerizing views of the north coast and the Nantucket Harbor.

The Tupancy family, who previously owned the property, used it to establish the first 9-hole golf course in Nantucket in 1921.

The golf course used to be mowed naturally by sheep and angora goats. The family kindly donated Tupancy Links to the Nantucket Conservation Foundation in the 1970s.


The Masquetuck Reservation is a small but picturesque conserved property with a size of just 13.5 acres.

It has short and easy trails, suitable for people with young children and those who want easy and brief walks.

Even though it will take you only about 10-15 minutes to walk the Masquetuck trail, it will take you through some beautiful spots, including a few salt marshes, a freshwater bog, an old hidden forest, and green meadows and grasslands.

You can admire the rare trees, plants, and birds there and the view of the Polpis Harbor and the beach below the reservation.

Squam Swamp

Located on Wauwinet Road, Squam Swamp has a picturesque walking trail that is 1.75 miles long, suitable for a leisurely and quiet walk among the untouched nature.

The area is known for its freshwater bogs, hardwood forests, and vernal pools.

You can enjoy a peaceful walk through some of the few forests on the island made up of black tupelo, red oak, red maple, sassafras, oak trees, and more.

The walking trail is a loop that passes through boardwalks and over stumps and roots but is easy and short and suitable for children too. It can be completed in less than 50 minutes, even if you are not an avid walker or hiker.

Downtown waterfront walk

The Historic Downtown of Nantucket is one of the most remarkable areas on the island and one which has the highest concentration of pre-civil war houses, buildings, and streets.

It is also the place where some of the best restaurants, most exclusive shops, boutiques, and galleries are located too.

The best way to explore this historic area is to take the Downtown Waterfront Walking Tour. You can download a free online guide and an online audio walking tour so that you ensure that you don’t miss a single site worth viewing and find out more about the remarkable history of most of the pre-civil war houses, buildings, and places there.

The Waterfront Walk begins at Easy Street, where you will see the iconic 007 red row boat and the Killen dory.

Then you will head to the Opera House Club and Dreamland Theater Complex, which used to be famous “naughty” clubs, saloons, and restaurants in the pre-depression years. Some of the club members and guests of these historic establishments include President Roosevelt, Liz Taylor, Judy Garland, and hundreds of other local and national celebrities and political figures.

The walking tour will then take you to the Thomas Macy Warehouse, the oldest waterfront building on the island, and where the ancestors of today’s Macy’s retail brand first began their business.

After that, you can gawk at the mega yachts at the New Whale Basin Marina and at George’s Park.

The next stop is Petrel Landing, and if you happen to be in Nantucket during the scalloping season in October, you can watch and even participate in the local tradition of scalloping.

If you want to see some live scallops and critters, you can visit the Maria Mitchell Museum right next to it.

The final point of the waterfront walk is South of Main, known as SOMA, which is a conglomerate of historic brick buildings where all of the local electrical power used to be produced until the late 1990s.


Overall, no matter whether you want to take a romantic stroll, enjoy the nature and views of the island, or learn more about the remarkable history of the island, Nantucket has it all, thanks to its numerous walking trails, bike, and walking paths and other free and easily accessible locations.

Just remember to bring some comfortable walking shoes and flats for your trip to the dreamy island!