Top 3 things to do in Oyster Bay, Long Island, NY

 

Sagamore Hill National Historic Site

Growing up in the concrete jungles of New York City, I always found happiness venturing out to wide open spaces of the world beyond New York City.  Long Island was always that place.  Thanks to my childhood buddy of mine Jimmy, who lived in Hicksville, I was fortunate enough to visit beautiful places like Oyster Bay, whenever we hung out.

Oyster Bay is tucked away on the north shore of Long Island and is located about an hour away from New York City.  A popular route into Oyster Bay is via Route 106 which is accessible from any of the major highways, the I-495 (Long Island Expressway), or the Northern State Parkway.  

Route 106 North takes you past Muttontown, featuring huge gated mansions, past Northern Boulevard, which is a major east/west route about 59 miles long from end to end, then past East Norwich, before entering the town of Oyster Bay.  

Oyster Bay is synonymous with Theodore ‘Teddy’ Roosevelt (the 26th President of the United States), as he lived and died there.  Although he was born in New York City, he made his home in the bucolic town of Oyster Bay.  Roosevelt’s love of nature is well documented, as he was the president responsible for creating the United States Forest Service, which established national parks, forests, game preserves, and bird preserves.

His conservation efforts are being widely enjoyed by millions of people every day.  My pack (myself, Mrs. Wandering Money Pig, and our Pomeranian dog Toby) has certainly taken full advantage of the national park system in our travels!

You can’t miss the ‘Rough Rider’ statue of Roosevelt as you head into the town of Oyster Bay at Route 106 and Berry Hill Road.  In addition, the two of the top 3 things to do in the town of Oyster Bay, which we will be covering in this post, feature Teddy Roosevelt!  You cannot help but run across Roosevelt in some form or fashion in Oyster Bay.

Without delay, let’s go ahead and see our top 3 things to do in Oyster Bay!

     1.  Sagamore Hill National Historic Site 

A trip to Oyster Bay wouldn’t be complete without visiting the Sagamore Hill National Historic Site, which was Roosevelt’s home from 1885 until his death in 1919.  Roosevelt endearingly called it his ‘Summer White House’, during his tenure as the 26th president.  

Sagamore Hill National Historic Site is situated on 83 acres of natural surroundings and historic buildings.    Although tours of Roosevelt’s home is currently not available due to COVID-19, you can tour virtually via their website.  Park grounds, beach area, and all paths, however, are opened at this time.

The nature trail that leads you to a scenic water views of the marsh area and the beach (Cold Spring Harbor Beach) is highly recommended, as well as walking the entire compound to view the gigantic windmill and his home.  It is one of several places in Long Island that allow pets, and we were really thankful for that…

Be sure to visit the little farmhouse next to the visitor center to learn about Roosevelt’s love of farming!

The giant windmill
View of his home 

     2.  Theodore Roosevelt Memorial Park

This was a hidden gem!  I was searching for a place to stop by to eat our takeout food, hopefully with a view, and I found it!

This is a bayfront park that features a marina, a beach, picnic areas, and a playground.  Look for the Theodore Roosevelt Elementary School, then turn right immediately after that.  *Note:  right turn is only permitted during school days.  Look for the signage to confirm.

As we drove into the park, we were greeted by an expansive view of the bay.  We saw sailboats, kayaks, and people enjoying the beach area.  The views were awesome!

We enjoyed our delicious Italian food (seafood pasta, chicken parmigiana, shrimp fra diavolo) takeout from a nearby restaurant in town, then wolfed it down while being mesmerized by the view.  It was truly one of those moments in life when nothing else is needed or wanted…We had incredible food and incredible views equaling one happy family!





     3.  Charles E. Ransom Beach

My buddy Jimmy was the one who initially took me to this beach area in our teens.  I always had good memories of the beach area with its beach vibe restaurants and attractions.

The drive into this beach is an attraction all by itself.  The West Shore Road is the road you’ll take from the Theodore Roosevelt Memorial Park.  It hugs the bay and the views are simply amazing.  If you have time, walk along the pedestrian friendly pathway along the W Shore Road.   

Once you get to the beach, the beach area has pedestrian friendly walkways as well.  Main attractions are the Bayville Winter Wonderland and Bayville Scream Park.  Several dining options exist overlooking the beach area if you get hungry.

If you get to the beach early enough, look for a huge tree with a picnic table near the playground.  This is our favorite place to hang out at the beach.  The tree provides a shade which I’m always looking for…(I get really dark if I stay out in the sun…)

Note:  I usually visit this beach during off season.  During the summer months, depending on how busy the beach gets, you may not be able to find parking there.  Consider alternate parking options.



Oyster Bay will always remain one of my favorite places of all time.  Whether that’s due to my personal bias for this place since my early teens or not, the beauty surrounding the town of Oyster Bay is 
undeniable.  I will always remember the fun times I’ve had with family and friends!

Thank you all for reading!

Jake

Wandering Money Pig 


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