Tramping The Trustees

Two years, 128 properties. Can we do it?

What is Tramping the Trustees?

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We’re Nikki and Mike. We like setting goals that get us out of the house. Several years ago, we visited 40 wine appellations over the course of a year.

We’ve enjoyed our membership with The Trustees, so much so that we decided to visit all the properties. And then we looked in December 2024 and discovered…The Trustees has 128 properties! Whoa!

We spent a few days trying to figure out how we could visit all 128 properties in a year. Some are colocated — heck, there are four properties at Crane Estate! (If you’re counting: Castle Hill on Crane Estate, The Inn at Castle Hill, Crane Beach on Crane Estate and Crane Wildlife Refuge on the Crane Estate.) But we quickly realized that in order to pull it off, we couldn’t get sick, we couldn’t travel anywhere that wasn’t a Trustees property, and if there was a natural disaster that shut down most Trustees properties for a few weeks, we’d be sunk.

This is supposed to be a fun project. Why be hard on ourselves? We decided to spread our excursions out over two years.

And, as we researched, we made another decision, too.

The Trustees Lodgings

The other thing we realized is that five of the properties are lodgings. Two are fiercely fought-over campgrounds (Tully Lake Campground and Dune’s Edge). Two are hotels that would be a serious splurge for us (The Inn at Castle Hill and the Guest House at Field Farm). And one, Long Point Cottage, runs about $7,000 per week. We could get it for $2,500 a week in the low season…but that is still waaaaay too rich for our blood.

Because we’d planned our adventure as largely day trips, because we cannot afford to spend $7,000 on a week-long house rental, and because booking the campgrounds is apparently a big challenge, Trustees lodgings are not part of this project. We will make it to as many as possible because they absolutely set us to daydreaming. Long Point Cottage is looking darn unlikely, alas. (Unless you, dear reader, are planning to rent it and have an extra bedroom? Hit us up.)

2 Years, 123 Properties

We finally landed on our goal. Two years, 123 properties. Totally doable, and it will get us to every corner of Massachusetts. And it also allows us to revisit properties, if we want to see them in a different season.

Of course, The Trustees could add new properties in 2025 and 2026 which will change this number! Stay tuned!

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