Penn To The End – Bike Ride

The Idea

“Penn to the End” is a 140 mile bike trip beginning at Penn Station and ending at Montauk Point Lighthouse. For those that know me – I’m a big fan of kooky ideas. So given my prior history, I was expecting Kerry’s reaction to be less than receptive. However, after checking schedules, potential campsites, and weather forecasts the trip got a thumbs up!

Two Points of View

Initially, I was initially going to bike camp this trip which would have made this adventure a lot rougher on me.  However, the stars aligned and I had the best support crew on board for this adventure.  We each recorded our experiences during this trip for this video. Enjoy!

Why am I doing this?
About 1 year ago I was diagnosed with high blood pressure, pre-diabetic, high-cholesterol, and overweight.  I was super stressed out and had to change things fast.  I needed to find a way to keep myself on a healthier, more positive lifestyle and decided that biking was the way to do it.  I began to bike commute to work as much as the weather would allow, I ate healthier, and worked on adopting a healthier attitude in life in general.  I recently had my annual physical and I’ve lost about 15 lbs, my bloodwork results were greatly improved, and my blood pressure was finally at a normal/safe level. All of this is still a work in progress and I guess this ride was a kind of celebration of being on a better, healthier path..

DAY 1

Total mileage for this trip is 140 miles.  We had it broken up into two days: Day 1 would have me bike from Penn Station NYC to Indian Island Point Campground which is about 85 miles.  My planned stops were Cunningham Park in Queens. Followed by Tanger Outlet in Deer Park NY for lunch with Kerry, and then ending Day One Indian Island Campground in Flanders, Riverhead NY.

We couldn’t have asked for better weather as the average temp was about 50 degrees.  The wind was at my back for almost all of this trip which significantly helped my endurance and morale.  

Here are the down and dirty deets of the areas I rode through:

• NYC piece of cake – lots of fun especially since traffic was light due to time of day
• Nassau County – Westbury was rough – had to ride on the sidewalk for 30 miles
• Suffolk County – Brentwood was also rough due to traffic and no shoulder but all in all pretty bike friendly
  

Support Vehicle

When Penn to the End was first imagined, I originally had the idea of biking to Indian Island with a bike camping setup.  That means that I would essentially have to carry ALL of my gear, food and water for this adventure.  No shower or bathroom facilities so things would have been  reaaaal interesting.  I mean – it’s been done by others so it’s not like I would be inventing a new way of camping. Although I thought that “roughing” it would be fun, I’m so glad that Kerry knocked some sense into me.  She offered to be the Support Vehicle which I’m very grateful for.

This was her first time doing the packing, hitching up the RV, and setting up camp all by herself.  She and I usually work as a team and split tasks.  This time she had to do it all by herself while I pedaled my way across Long Island.  

Kerry’s Point of View

Hi! This is Kerry, also known as Rick’s Penn to The End support crew. Ever since Rick and I bought Itty Bitty in February 2023, we’ve always done all the prep for travel together. That includes hooking up and towing. So this was my first time solo for all of that. And I’m happy to say it went great! We also had sunny weather for the trip, which was a big relief, because we had just gone through nearly a week of steady rain. I was tracking Rick as he made his way from the city and I met him at Tanger Outlets in Deer Park for lunch.

Lunch is over – back to riding!

It’s Rick again! I can’t begin to explain how much I appreciated meeting up with Kerry during this break.  Having lunch with her and refueling for the 2nd half of the day’s ride was the boost I needed to complete Day 1. NYC to Tangers Outlet was about 50 miles but I still had another 35 miles to ride until the Indian Island campground.  What you are seeing now is Kerry’s point of view as she drove to the campsite.  I will be providing a biker’s point of view of the entire trip in a later video.  

DAY 2

Total mileage for Day 2 was 50 miles.  Weather was a bit warmer and the wind wasn’t bad at all.  My main concern was how hilly the ride was from Montauk village to the lighthouse.  My only stop that day was to meet Kerry for a quick refuel about 6 miles before the climb to the lighthouse.  Although challenging, I was able to get up those hills and complete the ride. 

The last time we camped out on Eastern Long Island was our Wildwood visit last June and before that, we visited Hither Hills State Park in May of 2023 right before the memorial day holiday.  Both of these videos can be found on our channel’s Season 1 playlist.  So check them out when you can.

Kerry was now heading to Indian Island campground which was the only RV park in the area open for camping.  It was actually the ideal camp spot for this adventure as it positioned me for a solid 50 mile ride to Montauk for Day 2.  After Day 1’s 85 mile ride – another 50 didn’t seem so bad. 

Kerry found us a great pull-through site and set up camp to await my arrival.  I can’t stress this enough – knowing that she was waiting there with our RV was motivation enough to keep me biking strong.  The fact that steak and potatoes was on the menu didn’t hurt either!  

To be honest, I wasn’t sure if this ride was going to happen at all.  Not because of the weather or anything like that.  The ride almost didn’t happen because I was looking for excuses for it NOT to happen.  Sometimes life’s best moments are just a negative thought away from not happening.  My advice to anyone who is interested in doing a ride like this is to first do your homework on the gear, route, and camping logistics.  Second – find yourself a great support crew.  And Third – get on your bike and ride!

I will always remember this ride for two reasons: 1. The loving support of Kerry and how she’s been my “ride or die” since our high school sweetheart days.  2. How absolutely beautiful Long Island is from a biking point of view.