[CLOSED] Postcard path (4 sites): 350th anniversary of US postal delivery system 1 October - 29 October 2023

:world_map: CITY/REGION: New York, Connecticut, Massachusetts
:calendar: DATE: October 1-29, 2023
:alarm_clock: TIME: any time
:pushpin: CARD LOCATIONS: 4 stops (with four separate cards!) along the historic Boston Post Road (from New York City to Boston) - specifically, the “Upper” Post Road / Pequot Path

:page_facing_up: PLAN:
Along this postcard path, which can be completed any time from October 1 to 29, attendees celebrate 350 years of US postal history and learn more about the vibrant people and communities at their center. The 4 stops along the path are small boxes hidden outdoors, akin to a geocache or letterbox, in a place with a key historical connection to the Boston Post Road / Pequot Path. All sites have easy, free parking for those driving cars, and the locations are also accessible via public transportation.


Simple clues on this event webpage lead “attendees” to each box. Inside each box is 50 blank event postcards and some free stamp goodies. Attendees sign/stamp into each of the cards, as they would do for a meet-up – except LEAVE THE CARDS IN THE BOX and message the host (me) a photo to confirm you did this. At the end of the month, I’ll retrieve all the cards and mail a batch of fully signed cards to each attendee who messaged me.

All are welcome. RSVPs are not necessary, although you are welcome to comment below if you are planning to find a box! It’s unlikely you’ll be meeting other Postcrossers in person, although people are certainly welcome to self-organize to find boxes as a group!

A brief history of the Boston Post Road, which will provide helpful background for this trail.

When the Dutch colonized the mid-Atlantic in the early 17th century, their correspondence traveled only via ship. Native American communities, particularly the Lenape tribe, established a reliable and affordable, Indigenous-owned-and-led overland postal transport system that was well-used (and lauded) by the Dutch and then by the English colonies (learn more).

In January 1673, responding to an order from King Charles II to improve communications between New York and the English colonies, NY Governor Francis Lovelace ordered rider Mathias Nicolls to depart from the southern tip of Manhattan to lay out a road to transport mail between Boston and New York. The rider reached Boston two weeks later. The road was not new; the colonial route occupied and displaced a well-established Indigenous (Lenape, Pequot, Nipmuc, Massachusett, and more) travel-way.

A month later, the first postal mail arrived in Boston from New York City via the Boston Post Road.

More post roads became established thereafter. See the colored-in routes in Herman Moll’s 1729 “Post Map”. The map’s legend, “An account of ye Post of ye Continent of Nth America,” describes weekly mail service to and from the 13 Post Offices, including “the 3 Great Offices: Boston, New York & Philadelphia”:

In 1732, the Mass. General Court established an international “post office” at Fairbanks’ Tavern in Boston, which would allow mail to travel between the colonies and overseas.

In 1737, Benjamin Franklin was appointed postmaster of Philadelphia, and in 1753 he was appointed by the Crown to serve as joint postmaster general (with William Hunter of Virginia) of all the colonies. During his tenure, Franklin made vital changes to the colonial postal system, including instituting milestones along post roads, establishing a dead letter office, and employing post carriers to travel with the mail at night.

The more accessible the postal system became, the more it was seen as a rabble-rousing endeavor. In 1774, the King dismissed Franklin as postmaster general for “actions sympathetic to the cause of the colonies.”

To fill the gap, newspaperman William Goddard quickly set up a Constitutional Post for the revolutionaries’ inter-colonial mail service during the Revolution. The colonies funded it by subscription.

In July 1775, Ben Franklin was appointed postmaster general by the revolutionary Continental Congress. In his brief remaining tenure as postmaster general, he solidified the Postal Service of the newly independent United States as the one we recognize today.

By 1789, 75 Post Offices and about 2,400 miles of Post Roads served a population of almost 4 million European colonists.

Before the advent of home mail delivery in 1863, enslaved African-Americans were often the primary mail transporters between homes and the post office. However, once enslavers in the South saw the power of the post (a well-planned uprising of enslaved people in Haiti pointed to the mail as an organizing factor), a federal law was passed in 1802 disallowing African-Americans from carrying mail or even driving a carriage that held mail. This law held until 1861, when William Cooper Nell, an African American abolitionist, was hired as a postal clerk in Boston – the first African American to hold a federal civilian post.

The Boston Post Road paved the way - so to speak - for the US Postal Service and for many of the country’s transportation “firsts,” including the first successful long-distance stagecoach service in 1783, and the first highways. It should not be forgotten that the nation owes these successes to many African-American and Indigenous people whose stories are generally eclipsed by a tidier history.

A different postcard at each site commemorates US postal history, World Postcard Day, women’s history, African-American history, and/or Indigenous People’s Day.

Now let’s get finding!
BOX 1: Indigenous Community Leadership in Postal History
Location: 220 Boston Post Rd, Rye, New York 10580 - the Marshlands Conservancy of the Boston Post Road Historic District


BOX 2: Colonial Roots of the Boston Post Road
Location: Post Office grounds, 1865 Main Street, East Windsor Hill, CT 06028
Time needed to find this box once you’ve reached the address: 1 minute


  • Navigate to the East Windsor Hills, CT post office, one of the oldest continuing post offices in the nation. If you’re driving, parking is very easy.
  • Standing in front of the post office, look to your left. The sidewalk runs parallel to the road. Follow it to your left, about 15 paces.
  • Stop at the large blue historical sign describing the colonial history of South Windsor. You’ll also see a brief mention of the Podunk people, an Algonquin woodlands tribe whose descendants live on today as members of many other tribes.
  • At the base of the sign, see all the lovely flowers and a big shrub planted there? On the right side of the sign, look around the back-side of the shrub and you’ll find the box hidden there.


BOX 3: Bad-A$$ Women in Postal History
Location: 47 College Street, South Hadley, Mass., Gaylord Memorial Library (across the street from Mount Holyoke College)
Time needed to find this box once you’ve reached the address: 1 minute

  • From the main road (Rte. 116), travel up a small hill to reach a large, rectangular student/faculty/staff parking area adjacent to the Gaylord Library. Continue to face away from Rte. 116. The Gaylord library will be on your right. On your left you will see the edge of the Mount Holyoke observatory.
  • Navigate to the far back lefthand side of that parking area, getting as close as possible to the observatory while still being in the parking lot.
  • Notice the small, dark fence/guard rail that runs along this far edge of the parking lot. Walk to the end of it - again, getting as close as possible to the observatory while still being in the parking lot.
  • From the end of the fence, take one large pace toward the observatory, keeping close to the brushy evergreen foliage by your knees.
  • Lift up the brushy evergreen foliage (a ground juniper) and you should see the box!
  • Please re-hide the box well!
  • I am an alum of Mount Holyoke College, which was founded in 1837 as the first college for women in the US. It is one of my absolute favorite places on earth. I hope you will enjoy the coffee shops, etc., in the Village Commons, and maybe also take a stroll around the incredibly beautiful campus! The Williston Library (modeled after Westminster Abbey) is definitely worth a visit for library-lovers, and so is the Odyssey Bookshop (featured in the World’s Greatest Bookstores postcard set) – both are within a 3-minute walk of this box!


BOX 4: African-American History in the US Postal System
Location: 300 N Harvard St, Boston, Massachusetts 02134: Library Park, behind the Honan-Allston branch of the Boston Public Library.
Time needed to find this box once you’ve reached the address: ~5 minutes

  • Go to the public park that’s immediately behind the library (Roy V. Mallone Park). It is a very small park that’s open daily, dawn to dusk.
  • In the park find the three leonine guardians (Rusty, Lionel, and Hermione). Look on their plaques and note what year they were installed.
  • From there, facing away from the library, see the hill on your left? Navigate to it and climb the spiral path (ADA accessible) until you get to the top.
  • From the top, remember the year of the lions? Remove the zero from that year to get a three-digit number. Use the compass on your phone to orient yourself toward that three-digit number as a compass bearing. (if you don’t have a phone/compass on you, turn around until you see a spot that falls between a white lamp post and a stair-rail)
  • Walk a few steps in that direction, until you reach a knee-high wall with shrubby foliage on the other side. Peer over the wall. Hidden within arm’s reach, in the bushes (there’s no poison ivy, I promise, but there are a few thorns so be careful!) is the box.
  • Please be discrete when finding, and re-hide the box well!
  • Note: This park is a 0.2-mile walk from a Boston Post Road milestone

Have fun, finders! Don’t forget to message me whenever you locate a box and sign the cards. You can also comment here about your experience! This is the first-ever postcard path and I’m super curious to hear how it goes.

Happy finding!


What an inventive meetup idea! I can’t wait for the clues! Thank you for “hosting”/planning!



Good luck:)

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I wish I lived on the east coast. What a cool idea! And thank you for sharing about the history of US mail!


Great Idea! :smiley::+1:

I would love to swap a meetup Card. :smiling_face_with_three_hearts:
Once the designs of the four Meeting cards are public I can tell you which one. :wink:


@CStar9 , you are incredible! Wish I lived closer!:heart_eyes:


what a interesting idea (im a geocacher as well) may have to figure something out like this for our area> :thinking:
going to have to bookmark this and keep an eye on it 3,000 miles away :slight_smile:


Love this! Count me in! Thanks for organizing such a creative ‘event’!


This is great! I’ll be doing this for sure.

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I did not know about this and I am glad I found it! I look forward to finding some boxes!!!

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Hello everyone!
I would be very interested in swap the four wonderful cards.
My offers:

Enjoy your Meetup and thank you in advance.

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I would love to swap.

My offers:

  1. Meetup Florianópolis - SC, Brasil

  1. WPD by Danieli Dagnoni (bigger size 15 x18 cm)
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So glad I stumbled across this. Will be fun.

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@CStar9 Hey C, just wanted to check and confirm if this is still a go. If so, will everything be all setup to do the run on October 1st?

@logicoverflow - yep! Cards are printed and ready to go. I’ll update this page with the clues to the boxes after I plant them all (in the coming week).

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@CStar9 Awesome, thanks! Plan to hit up the Boston meetup and want to try to hit all of them on the way back home to NY.

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The clues are now live, @logicoverflow @fionat @myravern @alarica76 @Laidlaw - well, actually it’s only the 3 boxes in CT and MA for now, due to extreme flooding at the NY site. Happy finding, Happy World Postcard Day, and please let me know if anything about the clues is unclear!


So looking forward to this-- I won’t be able to go until later in the month since it will involve an overnight trip-- but I’m excited!

Thanks so much for putting together this fun adventure,


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Love this! Wish I wasn’t on the other side of the country!!

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Doing an overnight road trip from central Jersey this weekend to hit these fantastic spots! Thank you @CStar9 for organizing such a fun and inventive Meetup!