New Shoreham, RI to Cuttyhunk, MA

Sunday, June 21, 2026

Departure: Champlin’s Marina & Resort (New Shoreham, RI) 7:30AM

Special Comments:

• Sadly, our departure day from Block Island, RI!
• This morning, I really didn’t feel like touching a line or fender. Somedays, UGH!
• Upon our departure, the vessel off our bow, the Captain stood in his cockpit to observe our departure as we passed within 2′. The day prior we had the dock hands running as he was suppose to be on the opposing dock. No issue!
• Noticing lots of recreational fishing vessels out here today.
• Mary & Ian (M/V Aegis, N4014) are in a distance behind us.
• In the voice of Dorothy (Wizard of Oz 1939 Film), “Toto, this isn’t home” as we notice traps set in 110′ of water.
• Shortly, upon our mooring field arrival we launched the tender to go ashore and explore. Had fresh Lobster Rolls for lunch (Cuttyhunk Lobster Shack). We were going to have the Raw Bar deliver dinner to us (Cuttyhunk Shellfish Farms) but in catching up with fellow MTOA members in the Flotilla we just picked up and ate on the dock along with the group. Complimentary MTOA ice cream (Cuttyhunk Ice Cream Shop).

About Cuttyhunk, MA:

• Average household income, $132,254.
• Average property sale price, $1,600,000.
• Best known for car free charm, natural beauty, and sport fishing.
• Bring cash as credit cards are not widely accepted along with the spotty signals and WiFi.
• Cars are not permitted on the island. Transportation is either by foot or golf cart.
• Covered with rocks and stones that are only found only in the mountains of New Hampshire and Vermont.
• Coast Guard station has not been active since 1964.
• Cuttyhunk is a “dry island’, meaning no alcohol is sold here.
• Cuttyhunk Shellfish Farms operates a floating raw bar that will deliver to your boat on mooring balls. Known to sell fresh shrimp cocktail and oysters.
• Formerly owned by the Slocum family (1693 – 1858).
• Fourth largest of the Elizabeth Islands.
• Has no full-scale grocery stores.
• Historically (1864), powerful New York gentlemen purchased (1865) a large portion of the island, and built 26 “fishing stands“, with a limited number of members (up to 65) with a $300 admission fee. Every member hired a Chummer to cast, catch, and clean the fish for $1 per catch. Cuttyhunk Fishing Club eventually gave (1880) the land to Cuttyhunk Church.
• Home to the​ only one room schoolhouse (1873) in MA, the Cuttyhunk School​ serving Kindergarten – 8th Grade. Had 1 teacher and 3 students (August 2009). After the eighth graduate in June 2019, it reopened as a Steam Academy, offering seminar-style programs in lieu of having full-time students.
• Island only accessible via your own boat, chartering a flight with Bayside Air, or M/V Alert II ferry operated out of New Bedford, MA.
• ​Island’s name derives from the Algonquin word​, Poocutohhunkunnoh, meaning “point of departure“​.
• Last stop of the Boston Red Sox World Series Trophy Tour (June 24, 2005).
• ​Late Bartholomew Gosnold​ (1571 – 1607), English Explorer ​arrived in 1602​.
• Late Presidents, Theodore “Teddy” Roosevelt Jr (1858 – 1919) and William Howard Taft (1857 – 1930) were known to stay and fish out of the Cuttyhunk Fishing Club.
• Lodging options (2): Avalon, the Inn on Cuttyhunk and Cuttyhunk Fishing Club Inn.
• Lookout Hill (Lookout Park) is the tallest spot, standing at 154′ above sea level. 
• Lyes between Buzzard Bay & Vineyard Sound.
• Only lighthouse structure was a stone oil house, currently without a door or roof.
• Residents livelihood: boat building, carpentry, and shellfishing.
• ​Said to be a “bass capital of the world“​, there’s record of 73 lb catch (1913 & 1967).
• Song, “Sitting Becalmed in the Lee of Cuttyhunk” featured in William Finn’s musical, A New Brain (1998).
• Summer resident population is roughly 400. Year round residents roughly 12.
• West End Pond is primarily used for shellfish farming.
• William Madison Wood (1858 – 1926) bought the Cuttyhunk Fishing Club interest on the island, along with any other land that was for sale. Desiring to create a summer retreat for his young children. Further inviting affluent friends to purchase properties there too. Descendants of many of the families who purchased property from Wood’s still summer on the island annually today.

Arrival: Cuttyhunk Outer Moorings Cuttyhunk Island, MA (Sunday, 6/21/26) 1PM

For Additional Details & Photos Checkout, 2026 Marine Trawler Owners Association (MTOA) Northeast Region Inaugural Port Call Flotilla.

Monday, June 22, 2026

Departure: Cuttyhunk Outer Moorings (Cuttyhunk Island, MA) 9AM

Special Comments:

• Departure Day!
• Approaching Falmouth, MA one can’t but to notice the beautiful houses along the shorelines.
• Gathered for the MTOA Docktails (5PM – 6:30PM) which got moved to the pavilion due to light rain.
• Dinner at Flying Bridge Restaurant (Falmouth, MA)

Arrival: Falmouth Town Marina (Falmouth, MA) 2:30PM

For Additional Details & Photos Checkout, 2026 Marine Trawler Owners Association (MTOA) Northeast Region Inaugural Port Call Flotilla.