New Haven, a city on Connecticut's coast, celebrated its 350th anniversary in 1988 with a year-long schedule of special events. There were three "anchor" events for the celebration: the "New Haven Celebrates New Haven" festival on the city's green (it included a parage around the green by members of each of the city's neighborhoods), "New Haven Skyworks," a special fireworks display on July 4th and "Our Children, Our Future," a city-wide conference that sought to address the problems and needs of the city's youth, as well as how things could be improved for them.
There were also multiple local festivals, public speeches and various entertainment events, including a special performance of Thorton Wilder's Pulitzer Prize-winning "Our Town" play and performances by the visiting Moscow Circus. Wilder was born in Wisconsin in 1897, lived briefly in New Haven, attended Yale University in New Haven and spent many years writing stories, novels and plays while living in neighboring Hamden, CT; he died in Hamden in 1975.
The celebration was planned and organized by New Haven 350 Cultural and Historical Association, Inc. ("Association"). The Association was formed to oversee the anniversary commemoration and was dissolved following the anniversary once it concluded its business in 1989.
In addition to its planning activities, the Association also created a variety of commemorative souvenirs that included books, posters, pins, apparel and a limited-edition medal. As New Haven had been issuing commemorative medals for its major milestones for 100+ years, the inclusion of a medal as part of the 350th anniversary was not a major surprise.
The history of New Haven - the Elm City - extends back to the earliest days of Connecticut. It was organized in 1638 as a separate colony under the leadership of Reverend John Davenport and Theophilus Eaton. The original settlement was known as Quinnipiac, being named after the local Native American tribe from whom the site was purchased under a contract that promised the English settlers would protect the Quinnipiac from the Mohawk and Pequot, two enemy tribes who had nearly killed the Quinnipiac off.
Just two years later, in 1640, the name was changed to New Haven ("safe harbor"} and it has remained such ever since. The city was originally planned using a nine-square grid layout by John Brockett; the grid-plan gives rise to New Haven's claim to be "the first planned city in America."
(Note: Savannah, Georgia makes a similar claim.)The New Haven Colony became part of the Connecticut Colony roughly two decades later, in 1664.
The obverse and reverse designs of the attractive medal are described in the trifold leaflet shown below, so I won't repeat the information here. I will say, however, that the designs recall the subjects of the city's earlier medals: city co-founder Reverend John Davenport on the obverse and the New Haven waterfront along with the "Great Shippe" in the harbor. (Read more about the design elements in the leaflet.)
The anniversary medals were designed and engraved by Paul Lantuch; they were struck by Medallic Art Company (MACO) which had relocated from New York City to Danbury, CT by that time. The 0.999 fine silver version of the 2" medal was limited to 100 examples; the medal shown is #36 - it is edge-numbered. The silver medal displays light antiquing. The bronze version was produced in higher quantity, though its availability in the marketplace suggests that the mintage was 1,000 or less. I do not see any antiquing of the finish on the bronze medal.
I have not yet located information regarding the issue prices of the two medals. but I would guesstimate that the bronze piece sold in the $20 to $30 range, with the silver medal having a price of $80 or higher.
1988 New Haven 350th Anniversary - Bronze Medal
1988 New Haven 350th Anniversary - Silver Medal - #36
1988 New Haven 350th Anniversary - Informational Leaflet from Bronze Medal
1988 New Haven 350th Anniversary - Informational Leaflet from Silver Medal

The historical content of the leaflet is the same for each medal; only the "Certificate of Authenticity" panel varies. To highlight the difference, I've presented both versions.
Medallic Art Company (MACO) Promotional Leaflet - Included with Each Medal

For other of my posts about commemorative coins and medal, have a look at:
Commems Collection.