Did You Know? The only Revolutionary War battle fought on the East End started with soldiers carrying whaleboats across a Southold beach in the dark. They rowed around Shelter Island, took Sag Harbor before sunrise, and lost no one.
There is a version of this trip where you leave early, hit three museums, photograph a lighthouse, and are back on the expressway by dinner. People do it every weekend. We are not going to tell you it cannot be done.
We are going to tell you what you will have missed.
This year Suffolk County is marking two hundred and fifty years of American independence with a passport trail, and twenty-nine of its stops sit out here on the East End. They are not clustered in a walkable district. They are strung across two forks, an island in the middle, one ferry crossing, and a good deal of two-lane road with farm stands on both sides. The gaps between them are not a flaw in the itinerary. They are the reason the history happened the way it did.
After the Battle of Long Island in 1776, the entire island fell under British occupation and stayed that way for seven years. Out here that meant timber cut off Shelter Island and shipped north to heat barracks. It meant a Cutchogue landowner who announced he would not raise his hand against his king, and lost everything he had for saying so. It meant families who left their houses and became refugees in Connecticut. And it meant one night in May of 1777, when a Continental force crossed the Sound in whaleboats, landed on a Southold beach, portaged over the sand into Hashamomuck Pond, rowed the length of it into Peconic Bay, slipped past Shelter Island, and hit Sag Harbor at two in the morning.
That raid is the spine of this drive. It crossed three of our five regions in a single night. You get to take longer.
Every stop, all twenty-nine. This is the full East End list, not a highlight reel. Two in Riverhead, nine on the North Fork, one on Shelter Island, sixteen on the South Fork and one out in Montauk.
Five regions, one road. Riverhead, the North Fork, Shelter Island, the South Fork and Montauk, strung along two forks that only meet at one end.
The passport is free to download. Get the pdf or order a physical book from Suffolk250.org, then collect stamps as you go. Nothing on the trail requires a ticket to the whole thing.
The order is yours. There is no start line. Pick the fork you can reach first and work outward.
Jump to a Region
Riverhead
Riverhead is where the island splits. That makes it the natural place to start, and the only place on the trail where the whole East End is still ahead of you rather than behind.
Riverhead Free Library, Riverhead – A passport stop and a genuinely useful one. The local history holdings run deeper than most visitors expect, and it is a comfortable place to sit down with the book and plan the next three hours before you commit to a fork.
Suffolk County Historical Society Museum, Riverhead – The county’s own collection, and the right first stop if you want context before you commit to the drive. Go in knowing nothing about the occupation and come out understanding why every stop east of here has a war story attached to it.
Local Tip: Riverhead is the last town on the trail with a full range of gas, groceries and places to eat, and everything east of here thins out. Sort all of that before you pick a fork, and sort it early, because most cars heading east funnel through this town and the afternoon backs up behind them.
North Fork
Nine stops on a single road, the most efficient stretch of the whole drive and the one where you will be most tempted to pull over for something that has nothing to do with 1777. Let that happen. The vineyards and farm stands are part of the argument for staying over.
1799 Jesse Tuthill House, Mattituck – A house that wears its date in its name, and a reminder that the generation who lived through the occupation was still building here afterward.
The Old House, Cutchogue – One of the oldest English houses standing anywhere in the state, and the home of a loyalist whose refusal to break with the crown cost him his land and his place here. The rare historic house where the story is not flattering and the museum tells it anyway. If you only have time for one stop on the fork, this is it.
Horton Point Lighthouse Nautical Museum, Southold – The lighthouse came much later than the raid, but the bluff and the water below it are the same ones the Continental force crossed on the way to Sag Harbor. The climb is worth it for the view alone, and the beach at the bottom of the stairs is worth the rest of the afternoon.
Southold Historical Museum’s Maple Lane Campus, Southold – A cluster of buildings rather than a single house, covering the town’s long run through the war years and the occupation that followed. Also a stop on the North Fork Revolutionary War Trail, so the Revolutionary material here goes deeper than at most sites this size.
Southold Indian Museum, Southold – The stop that reaches furthest back. Everything else on this trail is a story about the last few centuries. This one is about the thousands of years before them, and it changes how the rest of the drive reads.
Brecknock Hall, Greenport – David Gelston Floyd built this house. His grandfather was William Floyd, the only man from Suffolk County to sign the Declaration of Independence. Grand, nineteenth century, set back from the road on grounds you can walk, and a good place to stretch your legs between Southold and the village.
East End Seaport Museum and Marine Foundation, Greenport – Maritime history a short walk from the ferry dock, and a North Fork Revolutionary War Trail stop. Build this one into the crossing rather than treating it as a detour.
Ireland House Museum, Greenport – Greenport’s own history, kept by the local historical society. Small and specific. Pair it with an hour walking the village afterward.
Oysterponds Historical Society, Orient – The last stop before the road runs out at Orient Point, and the reason to keep driving past Greenport. Orient is small, quiet and almost entirely unchanged. Twenty extra minutes each way, and worth every one of them.
Local Tip: Route Twenty-Five and North Road run parallel the whole length of the fork. Take one out and the other back and you will see twice the country for no extra time.
Shelter Island
One stop, two ferries, and a piece of the trail most people skip. Skipping it is how you end up with a version of the story that does not make sense. The island sits between the forks. That is why the raiders rowed around it in the dark, and why British crews came back to it again and again for its timber.
Shelter Island History Museum, Shelter Island – Housed in a family homestead that was already several decades old when the war reached it. The museum holds the island’s records, and that matters more here than it would elsewhere, because a nineteenth century fire destroyed the town’s earliest ones. One stop, but give it a real visit rather than a stamp and a turnaround.
Local Tip: Two crossings, one from Greenport and one to North Haven, and neither runs on your schedule. Treat the island as a half day rather than a pass-through and the ferries stop feeling like an obstacle.
South Fork
Sixteen stops, more than half the trail, and the only region where several of them are close enough to walk between. Sag Harbor is the place the raid was aimed at, and the village has never entirely stopped being a port town about it.
Westhampton to Bridgehampton
Greater Westhampton Historical Museum, Westhampton – The westernmost stop on the trail, so it is either your first or your last depending on the direction you are driving. Worth planning around rather than tacking on.
Pond House, Quogue Historical Society, Quogue – Quogue is the quietest village on this list and the Pond House is the reason to turn off the highway for it.
Water Mill Museum, Water Mill – A mill that gave the hamlet its name, and one of the few stops where you can see the machinery that actually ran a colonial economy.
Nathaniel Rogers House, Bridgehampton Museum, Bridgehampton – A landmark on the corner in the middle of the village, restored and now the Bridgehampton Museum’s front door. You have driven past it before without knowing what it was.
Southampton
Conscience Point Historic Site, Southampton – Where English settlers first came ashore on the South Fork. A marker, a view of the water, and not much else. The emptiness is the point.
North End Burial Ground, Southampton – A burying ground rather than a museum, and open air, so it works when everything else has closed for the day. The names on the stones are the same ones on the road signs.
Pelletreau Silver Shop, Southampton – A working silversmith’s shop on Main Street, where an eighteenth century craftsman made the objects that furnished colonial life. It is still a shop, and that is the charm of it.
Rogers Mansion Museum Complex, Southampton – The Southampton History Museum’s main campus, and the hub the town’s other sites orbit. Start here and the rest of the village makes sense.
Southampton African American Museum, Southampton – A restored barbershop on the corner it always stood on, now a museum of the community that used it. One of the newest sites on the trail and one of the most specific.
Thomas Halsey Homestead, Southampton – One of the oldest English frame houses in the state, and a different kind of old from The Old House up on the North Fork. Built by a family that was here almost from the beginning of the settlement.
Sag Harbor
Custom House, Sag Harbor – The house of the man who collected duties when Sag Harbor was a federal port of entry, kept as a home rather than staged as an exhibit. A small building doing a small thing well.
Heritage House, Eastville Community Historical Society, Sag Harbor – Eastville was a community of African American, Native American and immigrant families built around the whaling industry. This is the stop that keeps the harbor’s story from being only about ship owners.
Old Whalers’ Church, Sag Harbor – Later than the Revolution and worth stopping for regardless. The scale of it tells you what this harbor was worth once the war was over.
Sag Harbor Whaling and Historical Museum, Sag Harbor – The anchor stop on the South Fork. The whaling collection is the headline, but the building sits in the village that spent seven years under occupation and one night out from under it.
East Hampton
Guild Hall, East Hampton – The outlier on the list, and a reminder that the East End’s history did not stop in 1783. A century and a half after the war, this is where the artists who had been coming out here built themselves a permanent address.
Mulford Farm, East Hampton – An eighteenth century farmstead on the village green, with the rest of East Hampton’s historic core within sight of the front door. The single best stop for understanding what daily life looked like out here during the occupation.
Local Tip: Sag Harbor is a park-once village. Southampton looks like one on the map and is not, with its six stops spread over five miles. Plan the driving there rather than discovering it.
Montauk
One stop, and the longest drive between any two points on the trail. After a day of house museums and village greens the change in landscape does something useful. The land opens up, the trees go sideways, and you understand why this end of the island was grazing country long before it was anything else. East Hampton’s proprietors drove cattle and sheep out here every season and built keepers’ houses along the way to manage them.
Third House Nature Center, Montauk – The last stop east, set in the county parkland behind the village and named for its place in that old line of keepers’ houses. Third House has been a working building for most of the area’s recorded history, and the drive out to it through open country is half the reason to go.
Local Tip: If you have come this far, stay. Turning around at Montauk to drive back past every stop you already made is the single most common mistake on this trail.
Ways to Plan the Drive
Five ways to break twenty-nine stops into something a human being can actually do.
The Raid Route
Follow the 1777 crossing in order. Start in Southold, where the whaleboats came ashore at Hashamomuck Beach, just east of where the Horton Point Lighthouse now stands. The Sound and Hashamomuck Pond are separated there by a strip of sand about a hundred and fifty feet across. That short carry is the whole reason the route worked. Take the ferry and stop at the Shelter Island History Museum, on the ground the raiders rowed around in the dark. Cross to North Haven and finish at the Sag Harbor Whaling and Historical Museum. Four stops, one long day by car and ferry, and the only version of this trip where the geography explains itself as you go. Stay in Sag Harbor.
The North Fork Nine
All nine North Fork stops in two days, ending in Greenport on the first and Orient on the second. Wineries, farm stands and the Sound are on the same road the whole way, so the history stops carry the structure and everything else fills in around them. The only stretch of the trail where you can clear a third of the list without rushing.
Sag Harbor on Foot
Four stops inside one village, and the only cluster on the trail you can honestly do without moving the car. The Whaling Museum, the Custom House and the Old Whalers’ Church sit within a few blocks of each other, and Heritage House is a short walk out on Hampton Street. Half a day, and the most history per step anywhere on the East End. If you still have the afternoon, East Hampton is fifteen minutes away (when traffic is light) and its two stops share the same village green.
Southampton on Its Own Day
Six stops, and only two of them are on the same walk. Rogers Mansion and the Pelletreau Silver Shop sit a few minutes apart in the village. The Thomas Halsey Homestead, the North End Burial Ground and the Southampton African American Museum each lie in a different direction from the green. Conscience Point is out in North Sea, five miles off, and it is a drive rather than a detour. Give Southampton a full day and expect to park more than once.
The Whole Twenty-Nine
Six days if you want to see these places rather than tick them off. Two for Riverhead and the North Fork. One for Shelter Island and its ferries. Two for the South Fork, because Southampton needs a day to itself. One for Montauk and the long drive out to it. Most people who finish the trail do it as three long weekends spread across a season, one region at a time, and that is the better version anyway.
Where to Stay: Browse inns and hotels across all five regions on our Where to Stay page, and book on the fork you plan to finish on rather than the one you started from.
Before You Go
- Download the passport before you leave, not at the first stop.
- Check opening days directly with each site. Hours on the East End shift with the season and many of these are volunteer run.
- Admission varies by stop. Some are free, some are not, and none of them require a ticket to the trail as a whole.
- Conscience Point and the North End Burial Ground are both open air, so they are the two easiest stops to reach after hours.
- Build the ferry into your timing rather than around it. Two crossings, both short, neither on demand.
- Cell service thins out east of Orient and out toward Montauk Point. Screenshot what you need.
Quick Answers
What is the East End History Trail?
A free, self-guided passport trail marking Suffolk County’s 250th anniversary. It covers twenty-nine Revolutionary War-era sites across Riverhead, the North Fork, Shelter Island, the South Fork, and Montauk.
How much does it cost?
Nothing to join. The passport is a free download at Suffolk250.org, and a physical copy can be ordered too. Individual sites set their own admission, and some are free.
How many stops are there?
Twenty-nine: two in Riverhead, nine on the North Fork, one on Shelter Island, sixteen on the South Fork, and one in Montauk.
Do I need to visit the stops in order?
No. There’s no required order and no ticket for the trail as a whole. Start with whichever fork is closest and work outward.
How long does the trail take?
It depends on the pace. A few connected stops, like Sag Harbor’s four sites, fit into an afternoon on foot. Covering all twenty-nine comfortably takes several separate trips, most people spread it across a season.
Does the trail require a ferry?
Yes, if you’re including Shelter Island. Two short crossings connect it, one from Greenport and one to North Haven, and neither runs on demand.
A Note on the Distance
Twenty-nine stops are spread across eighty miles of road on two forks, some of them keep short seasonal hours, and one is behind a ferry. That distance is part of the history, not just the logistics. The forks stayed rural and exposed through seven years of occupation because they were far from everything, and that same distance is why a raiding party could row in at midnight and be gone by morning before anyone could stop them.
Planning the same drive without the museums? Our guide to the historic windmills of the East End follows a shorter version of the same road.
Find Your East End.