Fishing and Lobstering on the Other Casco Bay Islands: Long Island, Chebeague, Great Diamond, Little Diamond, and Cliff Island

Chebeague Island: A Real, Named Lobstering Identity

Of these five islands, Chebeague has by far the most documented lobstering identity. In 2009, Dropping Springs LLC launched Calendar Islands Lobster with support from the Island Institute, built explicitly as "the premier brand for lobsters caught by conservation-minded lobstermen in Casco Bay." It was structured as a fishermen-owned, vertically integrated cooperative, led by John Jordan, and grew to 29 participating fishermen -- doubling in its second year -- staffed largely by Chebeague Island residents. The cooperative invested in lobster-holding tanks, leased a Portland wharf, and ran a smack boat for distribution. That is a real, sourced 2009-era founding effort; this page states it as history, not as a confirmed currently-operating business, since its present-day status was not independently pinned down in the original research pass.

A fresh search for this project turned up something worth adding carefully: a company called Calendar Islands Maine Lobster shows up today with a Portland Fish Pier address, a Better Business Bureau profile, a FishChoice listing, and an active Facebook page, describing itself as a supply-chain partnership between Maine lobstering families, chefs, and dockside processors, with a longtime vice-president of sales who has represented it at international seafood trade shows. Whether this is the direct continuation of the 2009 Chebeague-launched cooperative, a rebranded successor, or simply a similarly-named separate company was not fully confirmed -- the name overlap is close enough that it is worth noting, but not close enough to state as settled fact. Separately, a distinct business styled Chebeague Island Lobster Co. (or Chebeague Lobster Co.) also turns up in business listings and on Facebook; its current operating status likewise was not independently verified. Anyone trying to buy from or work with any of these needs to confirm directly which entity is currently active.

Fresh reporting also surfaced a specific, named current lobsterman: Captain Alex Todd, described as a multi-generation lobster fisherman from one of Chebeague Island's oldest fishing families, working out of Casco Bay aboard a boat named for his sons, with Josh and Jake Todd both part of the operation. Coverage of the Todd family's lobstering has appeared in The Maine Mag and in video features tied to the Calendar Islands Maine Lobster brand. That is a genuinely specific, named, current-feeling data point for Chebeague -- but as with any small island fishing family, roles, boats, and business affiliations can change, so treat the details as a real starting point for further checking rather than a fixed, permanent fact.

Long Island and Cliff Island: Real but Thinner Threads

Long Island's relationship to the water runs deeper into its history than its present: before tourism became the dominant industry after World War II, the island's economy relied on farming, fishing, and lobster catching. That is a real, sourced historical fact, not a claim that lobstering is Long Island's leading industry today. No current lobster-license count, boat count, or named individual lobsterman for Long Island was found in either the original research or this page's fresh search -- that is a genuine gap, and this page is not going to paper over it with invented specifics.

Cliff Island's connection to fishing is more current: lobstering is documented as part of the island's present-day employment mix, alongside local island businesses and residents who commute to the mainland for work. Cliff Island is also, separately, the most remote of these five islands -- the longest Casco Bay Lines run, at roughly 60 to 120 minutes one-way -- and the only one of the group with entirely unpaved roads, which shapes how residents get gear and catch to and from the water. As with Long Island, no named Cliff Island lobsterman or specific boat count was independently confirmed; a fresh search for current Cliff Island lobstermen did not turn up anything beyond that same general employment reference.

Great Diamond and Little Diamond: An Honest Gap

Great Diamond Island's best-documented identity is Fort McKinley and the Diamond Cove redevelopment -- a former coastal-defense post turned private residential community, with Diamond's Edge Restaurant & Marina as its one notable waterfront business. Little Diamond Island is smaller still: a handful of year-round residents, a winter water shutoff, and a character built around near-total seasonal vacancy. Neither the original research nor a fresh round of searching turned up any documented current lobstering activity, named fisherman, or charter operation specific to either island. That absence is itself worth stating plainly rather than filling in with a generic "of course there's lobstering here" line -- these are genuinely thin, small, heavily seasonal communities, and this page is not going to invent an identity for them that the record does not support.

Recreational Fishing and Charters in Casco Bay

Beyond the working lobster fleet, Casco Bay as a whole carries a general, long-standing reputation among Maine anglers for species such as striped bass, mackerel, and other Gulf of Maine fish that move through the bay in warmer months. A fresh search turned up a real cluster of charter operations working these waters -- based out of Portland-area ports like South Portland, Falmouth, and Freeport rather than any of these five islands specifically -- offering trips for striped bass, mackerel, cod, haddock, pollock, and even shark species further offshore, generally running spring through fall with July as peak season. None of these charter listings singled out Long Island, Chebeague, Great Diamond, Little Diamond, or Cliff Island by name as a destination; they describe Casco Bay broadly. That is worth knowing if you are planning a fishing trip timed around a visit to one of these islands: the charter fleet operates in the same bay, but boards mostly on the mainland side, and you should confirm directly with any operator whether island-adjacent stops are part of what they offer.

This page also is not the place to state current bag limits, size limits, season dates, or license fees for striped bass, mackerel, or any other recreational species in Casco Bay -- those are set and updated by Maine DMR, and a general island page has no business guessing at figures that change from year to year.

Maine DMR Governs the Rules, Statewide Landings Context

Recreational saltwater fishing anywhere in Maine, including in the waters around these five islands, is governed by the state's Department of Marine Resources, which sets licensing requirements and species-specific rules -- size limits, bag limits, open seasons. That DMR holds this authority statewide is well-established; what specific limits or fees currently apply is not something this page will restate, because Maine DMR is the only source that keeps those figures current. The same goes for commercial lobstering: trap limits, license classes, and zone rules are set and enforced by Maine DMR, not by any general destination page.

On the broader landings picture: Maine's overall lobster catch was reported down again in 2025, a statewide trend rather than a Casco-Bay-specific one. Separately, a February 2026 Portland Press Herald story described an apparent lobster "baby boom" -- two straight years of above-average young-of-year counts, though still well below levels from two decades ago -- but that finding is specific to Lobster Management Area 512, covering Stonington, Vinalhaven, and Beals on Maine's central coast. It is not a Casco Bay finding, and this page is not going to borrow it to describe Chebeague, Long Island, Cliff Island, or the Diamond Islands, where no comparable young-of-year study was identified.

Before You Fish or Book a Trip

Put together honestly: Chebeague Island has the real, named lobstering story in this group -- the 2009 Calendar Islands Lobster cooperative, a possibly-related present-day Calendar Islands Maine Lobster company worth confirming directly, and a documented current lobstering family in Captain Alex Todd and his sons. Long Island and Cliff Island have genuine but thinner threads -- lobstering as a real part of their past or present economy, without named boats or license counts to point to. Great Diamond and Little Diamond simply do not have a documented current fishing identity, and this page says so rather than inventing one. Layered on top of all five islands is the same general Casco Bay recreational fishery -- striped bass, mackerel, and more, served mostly by mainland-based charter operators -- and the same Maine DMR rulebook that governs licenses, limits, and seasons everywhere in the state.

Before you fish, lobster, or book a charter anywhere near these islands, verify current recreational license requirements and species rules directly with Maine DMR, and confirm the operating status of any specific lobster company or business named here before relying on it -- small island fishing businesses can change hands, close, or rebrand faster than any general page can track.