Gloucester, MA to Kittery Point, ME

Monday, July 6, 2026

Departure: Ocean Alliance Docks (Gloucester, MA) 7:30AM

Special Comments:

• Gray skies and cool temperatures as we departed.
• Ocean looks smooth but has a seesaw punch.
• I found this interesting…Thacher Island Twin Lighthouses (aka: Cape Ann Light Station) (Rockport, MA) are the only operating twin lighthouses in the USA. Measuring 124′ tall these granite towers are exactly 300 yards apart. Aligned precisely on a north-south axis, when mariners see them perfectly in line, one could easily determine true north to navigate Cape Ann’s dangerous ledges. Built in 1771, and rebuilt in 1861. First station in the USA to mark a navigational hazard rather than a harbor entrance.
• Conditions are smooth and favorable. But, where is everyone?
• While underway, Jacques called ahead, no mooring balls available so we’ll be swingin’ on the hook.
• On starboard, we passed Isles of Shoals which is a strand of islands that separate the border of Rye, NH and Kittery, ME.
• We observed a catamaran struggling to anchor, tried along our port, stern, and starboard for over a hour. Eventually, they gave up and hailed the Harbormaster for a mooring ball.
• Apparently, on July 4th the was a Humpback Whale sighting here at Pepperrell Cove. WOW, hoping I can be so lucky!

About Kittery, ME:

• Approximately 1,007 residents (2025), function​ing as a stable, tight-knit, year-round community. 
• Attractions: Fort Foster Park​, Fort McClary State Historic Site​, Kittery Historical ​& Naval Museum​, Rachel Carson National Wildlife Refuge​, and Spruce Creek​.
• Average annual household income is $149,058​ (2025).
• Average residental purchase price, $663,500 (2025) with a suggested premium Kittery Point neighborhood average​ between $830,000 ​- $850,000​.
• Bistro 1828 at Pepperrell Cove Restaurant (Kittery Point, ME) is a local hub for boaters. A multi-level waterfront destination, the Ski Club Bar on the 3rd floor offers panoramic vistas of the cove and Ft McClary.
  Chauncey Creek Lobster Pier (Kittery Point, ME)​ on Chauncey Creek, this considered an iconic waterfront lobster shack with its own private floating docks. Tender friendly for enjoying a waterfront meal.
• First settled in 1623.
• Fort McClary State Historic Site (Kittery Point, ME), an active defense from the Revolutionary War (1775 – 1783) – WWI (1914 – 1918), and the former military base Fort Foster Park (Kittery Point, ME​).
• Frisbee’s Wharf (Kittery Point, ME)​ is a casual outdoor​ summertime favorite​ place.
• Home (1662) of late John Bray House​ is recognized as the ​state’s oldest standing ​property.
• Newcomen Society (1920) built a cluster of Tudor cottages as summer retreat.
• Popular for 17th​ Century​ (1601 – 1700) ​colonial architecture, coastal fortifications, and scenic ocean views​.
• Provisions at Pepperrell Cove open daily (8 AM – 6PM) offers essentials: beer, groceries, ice cream, homemade soups, made to order sandwiches, nautical gear, and wine. 
• Portsmouth Naval Shipyard (Kittery, ME), keeps the local economy active and stable through the winter, shielding it from being a total “ghost town“. 
• Safe Harbor Kittery Point (Kittery, ME) has a dedicated dinghy dock, complimentary for transient mooring ball guests. 
• Seapoint Beach (Cutts Island)is a beautiful curving stretch of sand bordered by a salt marsh.
• State’s oldest town​ (1647​).
• William Pepperrell Sr arrived from Devonshire, England as a lowly fisherman’s apprentice at the Isles of Shoals, NH. Eestablis​hing fisheries to supply the London​, England market​, buildi​ng a mercantile empire​ later inherited by his son. His landmark​ mansion at Pepperrell Cove ​is on the Piscataqua River.

Arrival: Pepperrell Cove Anchorage (Kittery Point, ME) 1:30PM (N43°04.800′ W70° 42.523′)

Next Stop: Unknown?