Calendar island hopping

I guess I took the month of August off. It was a hot one here on the island – and surprisingly busy with throngs of tourists putting around the island on golf carts from Mike’s and bikes rented from Brad’s.

We actually took this opportunity to venture off-island – only to head right back on-island and explore other parts of our watery backyard. Over the past month or so we’ve shipped off to several neighboring islands. Though only a few miles – or in some cases meters – away these islands seem like worlds of their own.  

Cushing’s Island

I felt like a real rebel (read: badass) pulling up to Cushing’s in my friend’s-friend’s Maritime Skiff. Cushing’s lies just beyond Sandy Beach and Catnip (read: poison ivy) Island – and taunts us Peaks Islanders with its dramatic cliffs that jut into the Atlantic. Taunt is an appropriate word because Cushing’s is a private island. While part of the City of Portland, the island is a summer colony that’s generally not open to outsiders. Luckily, we had an in. My friend’s-friend’s family has a house on the island – and welcomed us over for a socially distant hang.

I’ve always been keen to visit Cushing’s. Perhaps that’s because it’s so close, yet so inaccessible. Regardless of why, the visit did not disappoint. How remarkable is it to get picked up by a friend in a boat instead of schlepping it from Brooklyn to the UES on the subway or jumping in a car to say hi to a buddy in suburbia? These are the moments I just stop and pinch myself and say, “Wow – did that really just happen?”. Once on-island we meandered down the road – the one main drag that bisects the island like a synched-up belt – over to the friend’s family home and then down to the shore where the kids proceeded to get naked and go swimming.

We didn’t have a chance to make it to the far side of the island, the one with the dramatic cliffs – so another island jaunt is called for. A boat – and an invite – is all we need.

Cliff Island

Cliff is slightly more accessible than Cushing’s. The island got a major upgrade when it replaced its former name of Crotch with the more pleasant moniker of Cliff – but perhaps Crotch is more accurate. Not because of the unpleasantness of the island but rather its distinct shape. Cliff looks like a tangled-up H (source: Quinn’s favorite storybook) with a short, stubby isthmus that connects two distinct landforms.

Like Cushing’s, I’ve always eyed Cliff Island during my runs around the backshore. It’s about three miles from Peaks. So, Kellie and I hopped in Fogg’s water taxi with our bikes for some adventuring around Cliff. What Cliff seems to lack in, well, cliffs, it makes up for in solitude. Peaks can get crowded, particularly in August as I alluded to. Cliff. Just. Doesn’t. We took on the island, biking along the dirt roads and finding little pockets to explore further. My favorite discovery was along the southwestern tip of the island: a rocky beach with a serious tidal pool. It was a great vantage point to watch the coming and goings of the Casco Bay Lines ferries and crack open an Allagash.

Curious to learn more about Cliff? I’d suggest spending a morning with Cove Henry and his crew at the Cliff Island School. The Island Institute has pulled together a great vignette of life out on Cliff. Technically a member of the Portland Public School system, Cliff Island School only has a handful of students – four at the time of filming. The video does a good job articulating what it’s like to live year-round with a kiddo on the Casco Bay.

Long Island

I’ve jumped over to Long a few times. It’s one of our nearer neighbors – and like Peaks has a small community of islanders who commute into the city for work. During my most recent trip, we took out a friend’s skiff and anchored off of Shark Cove.

Those who have visited Peaks know that Sandy Beach isn’t always that sandy. In fact, Peaks’ Sandy Beach has quite a generous name for a little spit of shore with a very small seaweed-free section. Heading over to Long, however, puts Sandy Beach to shame. Andrew’s Beach, and the adjacent Shark Cove, feel like something out of the Caribbean. While the waters are much – and I mean much – colder than the bathwater off of the British Virgin Islands, there’s a similar vibe.

We weren’t alone with our idea to boat out to the beach – a few others had joined us. And yet, here’s the thing about Maine. Even when it’s busy, it’s not really busy. We spent the morning. Quinn and his friend Caroline conquered the shore, running up and down with abandon. He’s a lucky kid.

For those of you curious to get beyond Peaks and investigate the other Calendar Islands in Casco Bay, do it! There’s a lot – though less that 365 – for you to set foot on and enjoy responsibly.