To See or Not to See: Our Trek Down Long Island Sound

Well we had a plan - it was a good one. Leaving Montauk on September 16th, we had an itinerary in hand that allowed us to crisscross the Sound, enabling visiting of all sights and landmarks we were interested in, and new ones yet to be discovered. "HAHAHA," said the weather gods - "let's blow up a nor'easter and see how they fare." We ripped up the original itinerary, and improvised from there.

Greenport and Safe Harbor Stirling Marina - our first stop. We crossed Nepeague Bay into Gardiners Bay with no issue. The wind was a bit brisk at times, but it was a bright sunny day. Some sights along the way, including the Long Beach Bar Lighthouse, outside Orient Point.

The marina was lovely - smaller than Montauk, but excellent facilities (great showers). Given the cemetery across the street, our neighbours were very quiet!

Greg and I cycled out to Orient Point our first day there, a trip of about 20 miles when all was said and done. Given it is September, many shops and eateries are closed for the season, or only open on weekends - we were biking on a Tuesday. However we stopped at a lavender farm and had lunch at a Greek restaurant, both interesting stops. Travelling the main road to Orient Point revealed a different side to Long Island than noted in Montauk. Not as much money, much more of an agrarian presence, and a large shell fishing community. The ferry at Orient Point carries commuters from the mainland to Long Island, one of the main car ferries servicing the island.

We were finally welcomed to New York - the sign welcoming commuters exiting the ferry - something we missed coming in on our own boat!

Long Island is very environmentally conscious - watching over wildlife in particular. We saw many signs warning commuters about deer and turtles - although we did not encounter turtles on the roads during our travels, we certainly saw a large number of deer in every town we visited. The deer were not terribly frightened of cyclists, but it was hard to take their picture!

After visiting Orient Point, the weather forecast began to interfere with our plans. We had hoped to cross Long Island Sound and head to Mystic, CT for a few days before turning southward along the coast on our way to New York. Wind and wave forecasts influenced us to change course; as we could not stay in Greenport, we found a haven in Sag Harbor. Our last day in Greenport saw us cycling into the town - not as 'bougie' as Montauk but not without its own charm! In the bottom photos, although you can't tell, there is a large merry-go-round enclosed in the circular structure you do see on the town square. Sadly, we left on the eve of the annual Maritime Fest, held in this square and adjoining marina - an event eagerley anticipated by Greenporters each year, so we were informed by our marina neighbours.

Sag Harbor Yacht Club - our next 'port of call'. Although Sag Harbor is only two ferry rides away from Greenport (about an hour by bicycle), it was light years ahead in charm and amenities. This historical yacht club itself is lovely - well appointed and centrally located in the town. Our journey there was windy, but sheltered for the most part by Shelter Island (funnily enough). We certainly experienced 'small boat syndrome' at this club - oh the boats!! However, we got over it - quickly! We did stand out with our rear red lights in the evenings!

Again, the bicycles came out and we hit the road to explore the vicinity - Sag Harbor to Bridgehampton to North Haven over three days. Oh the homes we saw! This is where the rich and famous come out to play - after all, there is a Goop store in Sag Harbor for a reason. We certainly enjoyed the sights!

We met a lovely server at a French restaurant on our first day - Danielle - so friendly and helpful. Originally from France but a longtime US resident, she works summers in Sag Harbor then travels all winter. We had dinner there another night, purely because we enjoyed chatting with her so much - the food and service was great!! Some photos from Sag Harbor below - the signature sign from the historical Corner Bar, the windmill, Goldberg's Bagels, and other sights.

One highlight of Sag Harbor was the Whaling and Historical Museum (https://www.sagharborwhalingmuseum.org) - really interesting and enlightening - not a job either of us would ever aspire to given the gruesome tasks required of the whalers, not to mention the destruction of such large animals. The building was a masonic hall - the view up the stairs was the closest we could get to the meeting room upstairs.

Our trip to Bridgehampton left us with the impression that the Hamptons do not like cyclists as much as the rest of Long Island - perhaps a stretch of the imagination, but the roads in this part of the island left much to be desired for our safety and comfort. However we survived, and visited a winery on our travels. Although there are purported to be over 100 wineries on Long Island alone, it is hard to experience multiple tastings while cycling! We stopped at Channing Daughters Winery - a beautiful vineyard compound with some interesting sculpture/woodcarvings decorating the landscape. We tasted - we did not buy, suffice to say about the wine - but certainly enjoyed the ambience of the day.

A few more photos of North Haven to complete our time in Sag Harbor - a random statue garden alongside the road, the ferry to Shelter Island, and the beach. After prolonging our stay by one night in Sag Harbor due to ongoing weather and wave concerns, we finally made our move and headed to Branford, CT.

Safe Harbor Bruce & Johnson's Marina in Branford was our destination. Our crossing was not so bad - my PTSD from Martha's Vineyard was not revisited so it could not have been too bad! The sun was shining and the waves were mostly with us, as was the wind. Greg did segue into the Thimble Islands for a little tour - it is very rocky here so boaters must take great care as they navigate these islands. A few photos to share!

We only spent one night in Branford - it was enough. We had hoped to visit Yale University during our time here as Branford is very close to New Haven and we had originally been booked for two nights, but our loss of one night shortened our reservation time and was not enough to allow for this to occur. So, we spent our time watching football at the marina restaurant and bar - not a bad substitute plan! Another time perhaps....

Next stop - Harbor Point Marina in Stamford, CT, a three hour journey along the coast of Connecticut. Although we booked two nights here, hindsight would tell us that one night was enough. The marina is centered in the gentrified Harbor Point district of Stamford - highrises surrounded us, except for the cement factory next to the marina. Not much to see or do, especially in rainy weather. As this city is directly on the train route to NYC, it felt like a bedroom community for folks with jobs in NYC.

Lots of fowl to observe in the foul weather :). Cranes, Canada geese and swans - who would've thought?

We took the train to Norwalk, CT (the next city over, so to speak) as the main attraction in this area of Connectitut appears to be the Maritime Aquarium of Connecticut (https://www.maritimeaquarium.org). We learned a lot about jellyfish and Greg patted some of these as well as stingrays! Perhaps it is the September slowdown, but again not much going on in Norwalk. We did find a West Marine store - score! Lunch was procured at Donovan's (https://www.donovanssono.com), a bar with its beginnings in 1889 - Victorian in decor and very kitschy - not bad food either!

Our next stop was Port Washington and Safe Harbor Capri Marina, back on Long Island. The crossing was uneventful although the day was grey and a tad foggy. The marina is newish - we were back in the land of the 'big boats', with great amenities and restaurants. We did walk into the town, but the weather was not helpful! We were only here for one night - it was enough (starting to look forward to heading home). Some lighthouses on the way and the marina.

On Thursday, September 26 we left Long Island Sound for good (seeing Long Island Sound in the rearview mirror below) and entered the East River on our trek to the Big Apple and our official beginning to our Great Loop journey. More about that in my next post!