I was quite certain if I read closely enough I would find a requirement for an annual meeting in 23 MRS §3101-3104.  Having read the document three times and finding none, I believe the answer to your question is:

No, there is no legal requirement for an annual meeting.

The following statements (italics mine) give the right and the reason for road associations to hold meetings after the initial Organizational Meeting:

Section 3101, 2. Call of Meeting. The last sentence:  Subsequent meetings may be called in the same manner or by a commissioner or board appointed at a previous meeting pursuant to subsection 5. 

Section 3101, 4-A, Road Associations. A road association under this subchapter through its commissioner or board may address present and future repair and maintenance of a private road, private way or bridge as authorized by the owners at meetings called and conducted pursuant to this section until the association is dissolved by a majority vote of its members.

The Maine Private Ways Statute is painted with broad strokes. One of our Resources, Betsy Bowen's "Leadership Manual", 2009, Page 4, recalls a preamble to the Statute once considered by the Department of Environmental Protection (DEP) that stated:

"The intent (of the statute) is to provide a road association "template" to make it easier for landowners to form an association... . The DEP understands the wide variety of conditions under which road associations operate across the state. Some associations are large; some are small. Some have many seasonal residents; some have few. Procedures for assessing contributions have evolved in response to the conditions on that particular road and vary widely. The template must leave associations free to deal with their unique situations, but it must ensure that democratic procedures take place. "

Another MARA Resource, "A Guide to Forming Road Associations", DEP, 2014, page 19, states:

"For both statutory and nonprofit corporation road associations, you will need to have an annual meeting every year, since your officers, maintenance plan, budget, and assessment fee need to be voted on every year." 

Although the above statement does not confer a legal obligation, I agree with it ---as do the other owners in our road association. Our by-laws include this requirement, adding the right to levy a late charge and interest penalties on overdue maintenance fees and other directives considered necessary to supplement the provisions of the Private Ways Statute to ensure harmony and continuity of our road association and fairness in assignment and collection of maintenance fee shares. 

I am told by a District Court Judge that provisions of association by-laws (decided by the owners) weigh heavily in his decisions on owner disputes.

Roberta -

Your comments highlight the diversity of circumstances facing our road associations here in Maine. Last night I had an “ahah moment” while reading from Betsy’s “Leadership Manual” that caused me to revise my answer to the original question. (see above) I am struck by the implications of viewing the Maine Private Ways Statute (PWS) as a “template”. As I see it, if the PWS is a template, the products of this template:

1) immediately take on added legal significance, and, in use,

2) are meant to provide considerable freedom for road associations to adopt (or not) components, directives, and procedures necessary for governance in their unique circumstances. 

Where do we find the products of this template? 

We find products of the template in the written records of the various road associations who use the template as a guide. Certainly, one important piece of the written record is the association by-laws. Others include member correspondence and minutes of association meetings detailing events and owner decisions.

If I were a District Court Judge (which I’m not), after assuring myself that the road association was duly formed and operating according to the PWS, I would look first to the by-laws and then, for backup, to the minutes and correspondence to help me decide owner disputes.

The PWS as template concept helps explain unexpected lapses in content, as we have seen above, and permits owners to fill these gaps as long as the result is fair and equitable, and achieved through democratic procedures. The template concept supports the road association's right to provide the "definition of a parcel" in its by-laws and the judicious use of "late payment fees and interest" on assessments in default even though it is not addressed in the Statute.

I love this concept in case there was any doubt!