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In offering these updated comments, I’ve gone over the entire landscape again, with an effort to simplify things to make them easier for laypersons to follow. I’ve also corrected a numbering error in the original version.

Summary

Access restrictions, as applied to anyone who lives in Massachusetts, are flatly illegal under the principles articulated in Smith v. City of Westfield, which makes clear that all state residents have an easement to enter the area. An access fee is an interference with that easement, and since there is no other reasonable place for out-of-towners to park, a parking fee is an access fee. The seasonality of the restriction doesn’t make it legal. A legal case against parking stickers is winnable on a summary judgment motion, and therefore cheap and easy to bring. It’s reasonable, therefore, to expect litigation before long, and to expect to lose decisively.

Under the principles articulated in Leydon v. Town of Greenwich, access restrictions are very probably illegal under the First Amendment also, as applied to anyone, regardless of state residency. This case is more complex, because there are some issues of fact, and therefore more expensive to bring. Therefore, it’s reasonable to speculate that Orleans might be able to “get away with” charging a fee to out-of-staters. If a challenge is brought, though, Orleans is likely to lose.

My Qualifications

Let me start by qualifying myself: I graduated from the New York University School of Law, and am admitted to the New York State Bar, although officially retired. Because I prefer not to “spin” the truth, I chose a career in legal publishing rather than practice law. For over 40 years, I have contributed to pretty much all of the major national legal reference works used by lawyers and judges, as well as many state publications. At times I merely “refresh” existing coverage of well-settled law. At other times, I rewrite coverage from scratch to reflect new law or major changes to the law.

Measured by pages written and/or edited, I am the most prolific legal author in all of American jurisprudence, active or retired. I have been quoted at times in judicial opinions, most significantly by the District of Columbia Circuit Court of Appeals (the court Brett Kavanaugh, Merrick Garland once sat upon) in the 2020 decision, United States v. Carr.

 

By all of this, I don’t mean to suggest that I am Oliver Wendell Holmes, but I am not “just some guy,” either, and I think it’s fair to assert that if I see a legal problem, that creates a doubt worthy of careful legal investigation. As it happens, I see two serious legal problems with resident parking stickers at Kent’s Point, be they seasonal or year-round.

Hierarchy of Law

Let me make a fairly obvious point up front. The Select Board’s authority to regulate parking is subordinate to (1) the state and federal constitutions, (2) any federal statute which might apply, and (3) state statutory and decisional or common law. For instance, the Select Board can’t restrict parking to cars with “Jesus Saves” bumper stickers, or deny access to cars carrying female occupants who aren’t wearing burkas.

Seasonality Is Irrelevant

In terms of validity, nothing changes when we make a restriction seasonal rather than year-round. “The burkas are required only for a few months; they can wear what they want the rest of the time” isn’t a winning argument.

Other Towns’ Actions Are Irrelevant

Eastham’s parking restrictions at Wiley Park have no impact on any law which sits above parking regulations in the legal hierarchy. If Eastham had gotten sued and won, the rationale of that case might be helpful to the Orleans Select Board. In the absence of that, pointing to Eastham is like pointing to passing speeding cars when you’ve been pulled over – meaningless and futile.

Problem (1): Under State Public Lands Law, all Massachusetts Residents Have a Right to Enter Kent’s Point

Short Version:

Under Article 97 the Massachusetts Constitution, “The people” – of the entire state, obviously - have the right to the natural, scenic, historic, and esthetic qualities of their environment. Kent’s Point was purchased in clear implementation of Article 97. Orleans can’t take away the right of “the people” of Massachusetts to enjoy that land, and has no right to extort payment from anyone for exercising that right.

 

Long, More Legalistic Version:

One of several case which teaches us that everyone is the State has the right to enter Kent’s Point is Smith v. City of Westfield, decided in 2017.

 

The facts of the case are not exactly on point, but they don’t need to be. As the Supreme Judicial Court of Massachusetts works its way through explaining its decision, it lays down some foundational principles, citing its own historical opinions. These principles are “The Law” in Massachusetts, in a way that the court’s casual speculations about tangential matters (dicta) wouldn’t be, or that legal statements by the Orleans District court wouldn’t be. They are a pretty iron-clad guide to how Massachusetts courts are likely to analyze a case involving restrictions on public use of dedicated land.

The Smith case is mildly complicated because the court reviews three interrelated legal doctrines:

(A) Under the common law doctrine of dedication for public use, open space (such as we explicitly have in our case) is subject to an easement for public use upon proof that the owner has dedicated the use of these lands to the public (that’s in the Kent’s Point deed) and that the public has accepted the dedication through use of the open space (as has clearly happened at Kent’s).

(B) Under the common law doctrine of prior public use, public lands devoted to one public use cannot be diverted to another inconsistent public use without plain and explicit legislation authorizing the diversion. This doctrine is not limited to parkland, although it is applied more "stringently" where a public agency or municipality seeks to encroach upon a park.

 

(C) Under Article 97 of the Massachusetts Constitution, lands taken for the conservation, development and utilization of agricultural, mineral, forest, water, air and other natural resources (such as Kent’s Point) may not be used for other purposes (such as local revenue-generation) or otherwise disposed of except by laws enacted by a two thirds vote of each branch of the general court.

As to the relationship of these three doctrines, the court states:

There is no reason to believe that art. 97 was intended by the Legislature or the voters to diminish the scope of parkland that had been protected under the common law by the prior public use doctrine or the doctrine of public dedication. Such an interpretation would suggest that voters were hoodwinked into thinking they were expanding the protection of such lands … .
 

This means that the protection afforded to Kent’s Point under Article 97 includes the protections of the common law doctrines of dedication to public use and prior public use. Therefore, a decision under Article 97 has to be as least as favorable to public enjoyment of the area as a decision under the common law doctrines would be. This interconnectedness of Article 97 and the common law is underlined by the following sentence in the court's opinion:

Given this conclusion, we turn to the question whether the Cross Street Playground was dedicated by the city as a public park such that the transfer of its use from a park to a school would require legislative approval under the prior public use doctrine and, thus, under art. 97. (my emphasis)

That’s why these sentences from the opinion in Smith, based on Massachusetts common law, are completely applicable to our situation:

 

  The general public for whose benefit a use in the land was established by an owner obtains an interest in the land in the nature of an easement.

 

  The "general public" that has obtained an "interest in the land in the nature of an easement," is not simply the residents of the particular city or town that owns the parkland. (my emphasis)

 

  The healthful and civilizing influence of parks in and near congested areas of population is of more than local interest and becomes a concern of the State under modern conditions.

 

  Because the general public has an interest in parkland owned by a city or town, ultimate authority over a public park rests with the Legislature, not with the municipality. (my emphasis)

 

These statements of law are 100% fatal to the parking sticker proposal. Every Massachusetts resident is a member of the “public” to whom Kent’s Point is dedicated, and has an easement to enter the area. Under well-established legal principles an easement can’t be interfered with by the imposition of a fee. It’s the same as though you had an easement to drive over part of your neighbors’ driveway and they suddenly tried charging you a toll. At Kent’s Point, there is no adequate substitute parking to make it practicable to enter the area. Therefore, slam dunk for plaintiffs who challenge the ordinance.

The case would also be a very inexpensive one to bring. There’s no need for experts, for views of the property, for depositions, or any of that. The management plan states that Kent’s Point is an Article 97 property, Town Counsel has publicly stipulated to that, and the law of the Commonwealth as recently stated by its highest court is that all Massachusetts residents have an easement to enter. It’s a couple of sheets of paper, a motion for summary judgment, and everyone is home in time for lunch. So, the usual advantage that deep-pocketed wrongdoers have against mere members of the public does not apply. Sooner or later, someone will sue, and Orleans will get smacked down, with “optics” that will make us look greedy, elitist, and foolish.

 

What Does Town Counsel Say About Smith?

 

In an August 15, 2025 letter to the Select Board, responding to my Article 97/Smith-based challenge, Town Counsel conceded that Article 97 apples to Kent’s Point. However, he asserted that Smith would not apply to a sticker requirement because the Town “is not proposing to change the use of Kent’s Point to another inconsistent use,” since an area limited to Orleans residents would continue to be used for conservation purposes.

This is nice-sounding wordplay, based on an isolated phrase in Article 97, but it's inherently deceptive, as it uses "conservation" in a way that suggests purely environmental conservation, divorced from the right of people to "enjoy" the environment. Remember, the public trust in the Kent's Point deed is for conservation of "open space," which is a concept that includes recreation. Land ceases to be "open space" if people can't enter onto it and recreate. The fact that we're only keeping some people off the land is the same as requiring burkas only in some of the months of the year – legally irrelevant.

Additionally, Town Counsel's completely ignores:

(1) the continuing protection of the common law doctrines of dedication to public use and prior public use under Article 97, and the easement in the general public of Massachusetts which cannot be interfered with by the Town under those doctrines;

 

(2) the likelihood, in light of (1), that a court will consider fee-based stickers to be a partial “diversion” to a new use of “conservation plus income-generation;” and

(3) the alternate likelihood that the court will consider fee-based stickers to be within the phrase “or otherwise disposed of” in Article 97, which is vague enough to accommodate any change in the status of the land, such as income generation, if the court wants to construe it that way.

Bottom line, though, no matter how the court chooses to frame its opinion verbally, it’s not going to eradicate that public easement which was just explicitly recognized in 2017 by the highest court in the state, and which has roots back into the 19th Century. That’s a virtual certainty, no matter how much Town Counsel says, “never mind all that state policy stuff; just understand the phrase ‘inconsistent use’ the way Orleans wants you to.” Maybe the court would reconsider its precedents if there were some Earth-shattering emergency affecting the entire State, but “1100 cars a week go by my house, both ways, in the summer” isn’t going to be enough, and neither is “some of our fixed-income residents are getting hammered by property taxes, so we need to find some fees to impose on nonresidents.”
 

Thus, the Select Board cannot rely on Town Counsel’s casual assertion that Smith allows sticker-based access restrictions. If they want to go forward, they need an actual legal opinion, which addresses this issue squarely, and convincingly rebuts the arguments above. As a taxpayer, though, I would say “don’t waste our money.” There’s no chance, whatsoever – not because I’m a super-great lawyer, but because the case is a no-brainer.

 

Problem (2): The First Amendment and the Leydon Case

Because the Town’s case is hopeless under Smith, this is moot, except insofar as the Town might conceivably want to charge a sticker fee to out-of-staters, who are not protected by Smith. Leaving apart whether that’s a good look, there’s a chance they might be able to do that, but it’s not a very good one.

 

In the First Amendment realm, the most factually analogous case to Kent’s Point access restrictions is the Connecticut case of Leydon v. Town of Greenwich, involving nonresident access to a municipal beachfront park:

This case is not “binding” in Massachusetts, but in the absence of a highly pertinent Mass. case, it is “persuasive.” In other words, there’s a good chance that a Mass. court would follow the same logic in the absence of a good argument against doing so, especially since the Leydon case is heavily based on U.S. Supreme Court authority interpreting the First Amendment, as opposed to Connecticut law.

 

Leydon tells us that “parks” are “traditional First Amendment fora,” i.e., “places which by long tradition or by government fiat have been devoted to assembly and debate.” It goes on to say, citing Supreme Court authority, that the government “can exclude a speaker from a traditional public forum only when the exclusion is necessary to serve a compelling state interest and the exclusion is narrowly drawn to achieve that interest.”

Clearly, excluding all nonresidents is not “narrow tailoring.” So, to survive a Leydon challenge, Orleans would have to argue that:

(1) Leydon was wrongly decided; or

(2) Kent’s Point is not a “park,” meaning that the far more deferential “rational basis” test would apply.

 

Since Leydon is well stitched together by long-established judicial principles, articulated by the United States Supreme Court, it’s hard to imagine even trying to challenge its rationale. Town Counsel certainly has not done so. However, he has made his position clear that Kent’s Point is not a traditional forum, i.e., not a park.

To help us understand what a Mass. court will do to find the definition of the term “park,” which is not defined in the First Amendment itself, we have this from the Supreme Judicial Court of Massachusetts, in the 2019 case of Commonwealth v. Matta, 483 Mass. 357:

Because [the statute] does not define “park,” we give the term its “usual and accepted meaning[ ],” as long as it is “consistent with the statutory purpose.” (citation omitted) “We derive the words' usual and accepted meanings from sources presumably known to the statute's enactors, such as their use in other legal contexts and dictionary definitions.” (citation omitted). The term “park” is defined as “a tract of land maintained by a city or town as a place of beauty or of public recreation.” Webster's Third New International Dictionary 1642 (1993).

 

Kent’s Point is certainly maintained as a place of beauty, as well as public recreation. One can see the recreational aspect in the rules for the area, posted at the front.

 

Further, the fact that we “designate” Kent’s Point as a “conservation area” will mean nothing to a court deciding whether it is or isn’t a “park” for First Amendment purposes. One can’t avoid the First Amendment by labeling an area with words other than “park,” any more than one could avoid criminal liability for theft by calling it “a unilateral long-term loan.” Courts have seen people try to word-play with them a million times, and they routinely swat that stuff away and look at the actual facts.
 

Is there any help for the Town in the Kent’s Point deed? No. The public trust established by the Kent’s Point deed is expressly for “open-space-conservation purposes,” which is another way of saying, “for purposes of conserving open space.”

 

This does not mean that Kent’s Point is a wildlife refuge, like Audubon. Open space is commonly understood to include parks and recreation. Among the ample evidence of that is this statement from the Orleans 2025 Open Space and Recreation Plan:

Orleans has the rare combination of natural resources, open uplands, marshlands, and active recreation open spaces that work together to create a meaningful sense of place.

All of this means that if Orleans wants the court to decide that Kent’s Point isn’t a park, it is going to have to provide some persuasive evidence. Pictures of herons won’t do the trick. What will be important to the court is whether the area is a park “for First Amendment purposes,” i.e., whether it is a place “devoted to assembly and debate.” Note that in Leydon, at footnote 28, the court points to the plaintiff’s introduction into evidence of “copies of pamphlets distributed on the beach seeking to mobilize support and contributions for the town's legal effort, in conjunction with the association, to defeat the plaintiff's lawsuit.” This evidence mattered because it established that the area was a site for expression and debate. Plaintiffs in a case against Orleans would be able to introduce similar evidence in a challenge to this proposed ordinance, including the 2024 petition, asserting the “need to curb excessive use,” which was posted at the parking lot, as well as various fliers posted afterwards in opposition. In conjunction with ample evidence that Kent’s Point is the site of a thriving community, where people intentionally and regularly assemble in small groups and discuss issues of the day, these posting should establish that Kent’s Point is a “traditional public forum.”

 

Thus, unless and until someone can conjure up a solid argument for why Kent’s Point is factually and functionally “not a park,” (in its entirety, not just the now-inaccessible habitat areas) the Select Board should assume that it is.

What Does Town Counsel Say About Leydon?

Town counsel asserts that Kent’s Point is not a traditional public forum (which can be true only if it isn’t a park), and that therefore the “rational basis” test applies, rather than the “narrowly tailored” test. If he’s right, the court will accept pretty strained justifications for stickers, even if the judges are somewhat rolling their eyes. However, Town Counsel’s statements about all this have been vague and conclusory, and unsupported by caselaw, to the point that I would argue that they aren’t actually “legal opinions” as that term ought to be understood.

In a 2015 memo, Town Counsel said this:

Here, the Kent’s Point Conservation Area does not appear to be a “traditional public forum,” however, in discussing property security the Management Plan refers to “the development of a town park in the area,” so perhaps there is a possibility that any resident only rule could be challenged under the State and Federal Constitution.

Read that carefully. There is no law cited regarding what constitutes a park; the only evidence it provides (in the Management Plan) argues that the area actually is a park; and Town Counsel says in essence that “there is a possibility” that it may be a park. So, there is no way to read that as legal support for Kent’s Point being “not a park.” (Remember, if it’s a park, then it’s a traditional public forum, which means that the “narrowly tailored” test applies, which means that broadly-sweeping access restrictions are unconstitutional.)

In a 2024 memo, Town Counsel said this:

There would need to be a rational basis related to management in order to limit access to residents only.

No new legal basis for this is provided. So, so far all we have is the unsupported, and even somewhat contradicted, “does not appear” statement from 2015. In other words, nothing.

Town Counsel also said:

 

As noted in the 2015 opinion, it is possible that discrimination based on residency could be challenged as unconstitutional even with Town Meeting approval.

There’s an awful lot of hedging and vagueness going on here. Basically, it’s all “maybe yes, maybe no,” without any actual legal basis.

Then, in an update to Conservation Manager John Jannell which had to be in mid-2025, Town Counsel made this interestingly-worded statement:

My opinion does not conclude that Kent’s Point is a public park in the traditional forum sense.

Notice that he did NOT say:

My opinion concludes that Kent’s Point is not a public park in the traditional forum sense.

In other words, he admitted that he hadn’t expressed a conclusion on that. But then, he said:

There needs to be a rational basis for a resident sticker requirement …

 

He's just repeating the vacuous statement he made in 2024, but he’s also encouraging Mr. Jannell to push access restrictions through the Conservation Commission. This is like a dentist telling you, “I’m not saying there’s anything wrong with your tooth, and your x-ray actually looks pretty good, but you need an extraction.” I can’t speak to anyone’s intentions, but the impact of these communications has been (1) to indoctrinate the Conservation Commission into thinking they could legally recommend access restrictions, and (2) to give the members of the Select Board who want access restrictions “cover” for their actions, by deluding the public into thinking that restrictions are clearly legal. They are not.

Bottom line: A First Amendment challenge would a tough case for the Town of Orleans. However, it would be a more complex and expensive case for plaintiffs to bring than a Smith challenge, which, again, is a slam dunk. In theory, then, Orleans could try charging out-of-staters, who are not protected by Smith, and hope that none of them will bother to sue. Whether this is good policy, and worth the other forms of fallout it might produce,  is a whole other question.