The DL: The Village of Southampton, was settled in the 1600s by English Puritans, and became the first permanent English settlement in the State of New York. Today it is home to the 1% of the rich and famous and you can tell as soon as you step into the town. The crowd isn’t as young as somewhere like Montauk but you can find something for anyone in the group. Getting to Southampton takes around 2-2.5 hours from NYC. Here is a guide a weekend in in Southampton.
Guide to Southampton
How to get there:
- Option 1: Take the LIRR from Penn Station to Jamaica then transfer to the Montauk Line and get off at Southampton (this is what I have done before) – its one ticket not 2. You can also take the subway to Jamaica and catch the LIRR to the Montauk Line and get off at Southampton
- Option 2: Take the Jitney to the Southampton Station
- Option 3: Rent a car, if planning on spending more than a day or two I would recommend renting a car. I love being able to visit surrounding towns and explore places that aren’t the easiest to get to.
- There are a few smaller airports to fly into, you can come by helicopter from the City, but if flying commercial LGA is probably your best option and then renting a car.
Tip if taking LIRR: Once you get off the LIRR you can walk down Elm street to get to the main downtown or you can walk down North Main Street (don’t have sidewalks for a little bit of the walk). We walked one way in and one way out. Elm street you can see beautiful houses and North Main Street you can see more of the business and random restaurants and shops.
Where to Eat in Southampton
Breakfast and Coffee in Southampton:
- Tates, Hampton coffee company (out of the way if you are walking)
- Golden Pear
- Starbucks downtown if you must
- Four oaks cafe and juice bar
- Wishbone Farms
- Goldbergs (no real gf options but have açaí bowls)
- Southampton Cheese Shop
- One of the sit down restaurants on the main downtown strip.
For Lunch/Brunch in Southampton:
- 75 Main
- Sant Ambroeus
- Sip N Soda – casual diner feel
- Golden Pear
- Seans Places – sandwiches to go and bring to the beach (gluten free wrap options)
For Dinner in Southampton:
More Low Key Options
- Publick house
- Boa Thai (eat outside)
- Bamboo sushi
- Fellinghams sports bar
- Union Burger Bar
- Shinnecock Lobster Shack
- Coast Grill and Bar – Opened August 2021
Nicer Dinner Options:
- Blue mar
- Claudes
- Union Sushi and Steak
- Le Chef
- T Bar
- Le Charlot, Dopo Argento
- Tutto Il Giorno South
- Southampton Social – younger scene, dj, minimum spend
Need Groceries or something for the beach – there is also a Citarella, CVS, Stop and Shop, and a few liquor stores in the downtown.
What to do in Southampton:
Shop – some of my favorites
- Hildreths Homegoods
- Breezin Up – any Southampton gear you could want
- BookHampton – some of the best coffee table books here
- Tenet
- Love Shack Fancy
- Intermix
- Club Monaco
- Ralph Lauren here has cool vibes
Go to a Vineyard
- Wollfer Estate Vineyard is literally 20 minutes a way. Do a tour, wine tasting, picnic, attend a sunset event, or just drive by the wine stand and check it out.
- Duckwalk Vineyard in Southampton – haven’t had a chance to visit but its very affordable at $13 for 4 samples
Attend a Local Event
- I went to an antiquing sale and a free jazz concert that were happening in the town, make sure to check out the local calendar of events when visiting
Go to Southampton’s Cooper Beach
- How to get the beach without a car – you can uber ($20 each way from the downtown) or you can use circuit, which is a free electric shuttle, you just need the app.
- Parking is $50 per car and fills up quickly, the earlier you get there for the day the better and reduced pricing usually. Its a pretty far walk and not a lot of dedicated sidewalks from the downtown to the beach.
- There is also bathrooms, concessions, and showers to rinse off at the beach. You can rent chairs and umbrellas $15 each – cash only!
Visit a museum
- Southampton Arts Center
- The Parish Museum
- The Southampton History museum
Explore Nature
- Agawam Park (small park on the water by the downtown)
- Conscience Point Wildlife Refuge
Admire the Mansions
- Drive by celebrity homes if you brought a car or just explore the beautiful neighborhoods
Golf
- There are a few public courses nearby
Visit Neighboring Hamlets
- If staying longer check out my other guides to The Hamptons, like this one to Montauk
- You are so close to Easthampton, Bridgehampton, Hampton Bays, and Westhampton you can easily grab a meal or explore their downtowns.
When to Visit Southampton:
Memorial Day – Labor Day is peak season, for a more affordable stay go right before or after this. Fall is also a really nice season here.
Where to Stay in Southampton:
- Southampton Inn
- A Butler’s Manor
- Air BnB
If planning a day trip to Southampton, check out my guide.
Leave a Comment