Having lived in Greenwich for over a decade, I’ve experienced it both as a child and an adult. Despite growing up here, I didn’t fully appreciate its offerings until I returned as an adult. Many newcomers or day-trippers are unaware of the town’s hidden gems, given its primarily residential and private, but there is a lot to do for those just looking to visit as well. You just need to know where to look. And this is the right place. Drawing on my extensive time here, I’ve curated a list of things to do for visitors, first-timers, or returning visitors for the ultimate long weekend in Greenwich, CT (or longer!).
Are there multiple neighborhoods in Greenwich, CT?
Yes, the entire town is called Greenwich, CT, but within Greenwich there are multiple neighborhoods or communities. The primary 5 are: Byram, Cos Cob, Greenwich, Riverside and Old Greenwich. If we wanted to get even more granular there are more neighborhoods like Glenville, Chickahominy, Round Hill, Belle Haven, Deer Park etc. But for the purpose of this long weekend in Greenwich or longer, we’ll be sticking to the big 5.
How to get to Greenwich, CT?
If you’re not coming by car, it’s actually a super easy commute from the New York City for a weekend in Greenwich. That’s the primary reason Greenwich is an attractive place to live for people who work in New York. From Grand Central, you take the Metro North Railroad directly to any of the 5 Greenwich neighborhoods listed above. The train stops as Port Chester (for Byram neighborhood), Greenwich (at the bottom of Greenwich Ave), Cos Cob, Riverside, and Old Greenwich. From there you can walk to your stay if it’s nearby or Uber/Lyft. The commute is about 42 minutes if it’s an express train and 1 hour if it’s a local train.
Where to stay in Greenwich, CT?
As a local, there are 2 areas I would recommend to stay for a weekend in Greenwich. One is next to Greenwich Avenue. This will allow you the flexibility to go out for drinks or to eat during any time of the day, go shopping, head out to the island beaches at the bottom of the avenue, or even take the train to any of the other Greenwich neighborhoods. If you find yourself near Greenwich Avenue, you are in the center of the action. If you choose to stay on the Ave, there are 3 different options, each very unique from the other. I would’ve recommended the historic Thomas Henkelmann in Belle Haven at #1, but it’s closed for restoration unfortunately. So right after Henkelmann, we have:
The second area I would recommend you stay in is Old Greenwich, which is walking and biking distance to Tod’s Point. Finding properties here is much harder, but the benefit is that you’re right on the water.
Quick Navigation
Day 1
Day 2
Day 3
– Day 1 –
Morning: Sound Beach Avenue
If you’re visiting Greenwich in the summer, the first day I’d recommend you spend sometime in our beach neighborhood, Old Greenwich, more so than our main town, Greenwich. Old Greenwich is the highlight of the town in the summer because it’s just a few minutes from the Greenwich Point Park, also known as Tod’s Point Beach. More on that below. Old Greenwich is small, but in the summer it’s bustling. It’s tiny main street is called Sound Beach Avenue and it has a few restaurants, cafes, an ice cream parlor, breakfast spots, grocery stores, a local butcher shop, a hardware store, a yoga studio, and boutique stores to visit like Back 40 Mercantile, Originals Lifestyle, Fred Boutique, Abigail Fox Designs and Rummage Room.
For a more down-to-earth store with Greenwich inspired apparel, visit Chilly Bear. This is where I get a lot of my Greenwich branded apparel alongside ASF Promotions (located above Gofers on 551 East Putnam Ave). The town also has a bookstore, liquor store, an art gallery and a few other stores. It has it all if you think of it! It’s just very small. It’s worth going for a stroll and hopping in and out of shops. If you want to grab breakfast while here, I recommend you stop at Sweet Pea’s Baking Company or Joe Studio Café for coffee and Upper Crust Bagel.
Afternoon: Tod’s Point, or Greenwich Point Beach
What to Do at Greenwich Point Beach, Tod’s Point
Just a few minutes from Sound Beach Ave is Tod’s Point. It’s a 45 minute walk from the main street, so a car is recommended. However, there are a ton of caveats to this stop…Tod’s Point, is more than just your regular Connecticut beach. Unfortunately, it is a private beach for Greenwich residents from May 1 – October 31, but guests and non-residents can buy a $9 day pass and a $40 parking pass online (you need both) and join residents during the summer. If you show up without a parking pass or day pass, the gatekeeper will ask you to turn around so come prepared! Greenwich Point Beach is located on 147 acres and it’s much more than just a beach on the Long Island Sound with gazebos for shade and beach concessions. Venture beyond and you’ll find over 3+ miles of hiking trails, picnic areas, a yacht club, a beach made of only shells and a secret garden (good luck finding it! Fun fact: This is where I got officially married, before my big wedding ceremony in Italy). You can even take a sailing lesson, rent a kayak, sailboat, catamaran, or SUP, and more.
Afternoon: Rent Kayaks, Catamarans or Sailboats
What to Do at Greenwich Point Beach, Tod’s Point
Greenwich Community Sailing offers rentals during the summer for catamarans (for those with permits), kayaks, and stand up paddle boards. Prices vary anywhere from $25 to $60 per hour depending on what you are renting. Greenwich Community Sailing also offers children and adult sailing classes during the summer. So should you want to learn how to sail and receive your permit, just sign up for classes.
I highly recommend you try and see Greenwich from the water. From the inlet near the Old Greenwich Yacht Club, you’re able to kayak up close to the big multi-million dollar houses on the water. They’re breathtaking to see up close. You can even paddle as far out as Riverside Yacht Club if you’d like, but make sure you’re in shape and it’s not a rough day. Once you step out of the inlet, the water tends to get rough if it’s a wavy or high boat traffic day.
– Day 2 –
Morning: Bike Riverside
The activities aren’t over yet. Yes you walked and kayaked yesterday, but you also lounged on the beach so got to unwind. Today is a day full of new activities…biking and polo! This morning you’ll be exploring the neighborhoods of Riverside and Old Greenwich, but on bike. If you didn’t bring your own from home, perhaps your bed and breakfast has some available. Otherwise, I recommend renting from the only store in town that rents bicycles Bax Cycle, previously known as Dave’s Cycle. It’s located in Cos Cob right before the entrance into Riverside, so it’s a good location to rent them.
Bike your way into Riverside and enjoy a stroll through the residential streets while marveling at the fabulous homes and architecture. That’s one of the most fun things to do while in Greenwich since it is one of the wealthiest towns in the US! If you want to grab some breakfast before heading out on your bike ride, stop by one of my favorite’s Ada’s Kitchen + Coffee at the entrance to Riverside.
Some of my favorite streets to bike down include:
Morning: Old Greenwich Houses
Rather than lingering around Sound Beach Avenue, we’re now going to explore some of the private road and houses by the sea on the way up to Tod’s Point Beach. Along the way you’ll find a lot of small communal things that we do here in Greenwich. From communal libraries where you can take or leave a book, to communal toy areas for kids. There’s also private beaches along the way and my favorite of all is the kid’s lemonade stands in the summer. I always stop for a fresh lemonade along the way, so remember to bring cash! Although they sometimes accept Venmo too. Once on Sound Beach Ave, break off onto:
Afternoon: Greenwich Polo Club
Your Guide To Attending A Greenwich Polo Club Match
Whether you’re into polo or not, a Sunday match at the Greenwich Polo Club is a must-do summer experience for anyone in the tri-state area. My first-hand experience at the Greenwich Polo Club can be summarized in one sentence: A glamorous yet laidback outing for a day of men on horses, the cracking of the mallet, and time-honored traditions like the ritual stomping of divots at halftime. While the sport is fun to watch and is open to children, pets, and adults, the real entertainment is the people watching. Here is everything you need to know about attending the Greenwich Polo Club Match.
– Day 3 –
Morning: Walk Greenwich Ave
Greenwich Avenue, CT: What to Expect and Find
What do traditional traffic cops, award winning chefs, waterfront hotels and bars, high-end stores, classic car collections, and pop and contemporary artists all have in common? They can all be found on Greenwich Avenue. The town of Greenwich has a few main streets, but one reigns among all–Greenwich Avenue, or what us locals refer to as just ‘The Ave.’ It has been called by some the Rodeo Drive of the East in terms of the shops you will find mixed with its high-end and casual dining options. While the shopping may be a bit more on the expensive and upscale side, there are still plenty of reasons to visit the Ave. There are a few specialty designer brands and fast fashion stores accessible to all and dining is on par with New York City, making it an enjoyable mid-day activity and the perfect place to people and car watch.
Residents Only Opportunity: The Greenwich Town Party is an annual event open to residents only that happens every Memorial Day Weekend in Greenwich. The only way to attend is through an annual raffle. If you get selected, you can attend. Every year the festival has big headline names, from the Beach Boys to Mumford & Sons, Billy Joel, The Eagles, and the Zac Brown Band.
Lunch: Delamar
32 Amazing Restaurants in Greenwich, CT Right Now
The oh so famous Delamar. The place to see and be seen by all. It’s the only hotel located on the waterfront in the Greenwich marina. Yachts are constantly parked outside and it’s one of the trendiest lunch and dinner spots in town. It’s also the only dining location with a water view in Greenwich and one of the few in Fairfield County. L’Escale, which is part of the Delamar hotel, is the place to go for French fine dining. Order a bottle of their house rosé, their famed chicken paillard, and coveted crème brûlée. You won’t be disappointed.
Afternoon: Bruce Park Museum
This is a great rainy day activity. Robert Bruce, a wealthy textile merchant, owned this land before selling the deed to the town and establishing Bruce Park and museum in 1908. Exhibits change all the time, some include really cool trippy and pop art installations or exhibits like Dualities or Let In, Let Go, some classic Andy Warhols, science galleries that feature animals and dinosaurs, a minerals section and more. The exhibits change all the time so check in and see if something sparks your interest.
Afternoon: Bruce Park
We go from cultural to nature. Think on some of the art you just saw with a 3+ miles stroll and perhaps a picnic by one of the many ponds at Bruce Park. Next door to Bruce Museum, is this expansive park with beautiful, stunning homes and mansions you can walk by. There’s even a croquet field for those interested, but you’ll have to come dressed for the game and reserve a space online.
Evening: Walk Belle Haven
If you have the energy to continue your walk (perhaps after a quick snack on Greenwich Ave…) I recommend you head up hill past Greenwich Marina and towards Belle Haven. There isn’t anything to actually do in Belle Haven, as it is a residential neighborhood, but the neighborhood is a feast for the eyes. It’s home (no pun intended) to some of the nicest, grandest, and most expensive waterfront homes in Greenwich, CT. All you do is really just wander around and take in the mansions, there’s a lot of fun styles and architecture along the way. You will hit a standpoint when you come across the gated community. While some of Belle Haven is open to the public, the more elite areas are a gated private community. You have to know someone to get in. My usual walk is up Shore Road which turns into Smith Road. From here you can break out into the public roads such as Field Point Road before heading back to the Avenue.
– Day 4 –
All Day: Ferry to Islands
A Guide to Visiting Island Beach in Greenwich, CT
If you don’t have your own boat and your looking to get off the mainland, you can visit one of Greenwich’s 2 public islands accessible via ferry from the Arch Street Dock at the bottom of Greenwich Avenue. Island Beach is the most visited, followed by Great Captain Island. Plan a whole day on the islands since there is much to do and it’s a unique experience on the Long Island Sound. You can even camp on the island’s overnight…yep, you heard that right! Like all other beaches in Greenwich, guests and non-residents can buy day passes and/or parking passes online to get to the islands during the summer. The ride to Island Beach has to be one of my favorite things to do in all of Greenwich. From the ferry, you can see the Greenwich marina, sail by the Delamar and the beautiful Indian Harbor Yacht Club, and most importantly cruise by some of the stunning houses (or more precisely – mansions) of Belle Haven.
A Guide to Visiting Great Captain Island in Greenwich, CT
Unlike Island Beach, Great Captain Island isn’t as equipped as an island. It doesn’t have a concession stand, a lifeguard, and all the bells and whistles Island Beach has. It’s more rustic, more Robinson Crusoe-style with just a few picnic tables, grills, restrooms, a swimming area and a beautiful crescent-shaped beach. Most people use the island to anchor their boats near shore and just float around the area, so you’ll find it has heavy boat traffic, unlike Island Beach. From the beach, you can see the Manhattan skyline.
Night: Capitol Theatre
A Night at The Capitol Theatre, Port Chester
Right across from Byram in Greenwich, CT is Portchester, NY. One of the main attractions in Port Chester is the beautiful and old school Capitol Theatre. The Capitol Theatre is one of my favorite nightlife activities to do in the Westchester Fairfield County area. Not only do the shows start and end at reasonable hours, but the acts are big, the venue is intimate and iconic, and the tickets are very affordable. Some of the most recent acts Pat and I have seen (and who have played) at the Capitol Theatre include Daughtry, The Fray, Kevin Hart (we got to see a sneak peak of his new Netflix set before it was ever recorded or aired), John Mulaney, Nate Bargatze, Mark Norman, Dane Cook, Johnny Depp and Jeff Beck (featured in video above), Keanu Reeves and Dog Star, The Stix, Norah Jones, Bob Dylan, The Beach Boys, Tim Dillon, and there’s always ‘80s music reenactments, Taylor Swift nights, Queen tributes.
– Day 5 –
Morning: Byram Beach/Shore Park & Pool
We continue our Greenwich, CT beach hopping guide with a morning at Byram Beach. Same routine as all the other Greenwich beaches – buy a day pass + parking pass…yada yada yada. BUT, what makes Byram beach cooler than all the other beaches is that is has a public pool overlooking the Long Island Sound and tennis courts. Unfortunately, the only people allowed to use both the pool and tennis courts are Greenwich residents who have a seasonal Park Pass…but, the beach is still a lovely experience. Byram Beach has two small and intimate beaches overlooking the Byram beach marina, Belle Haven, and Great Captain Island, Shell Island, Bowers Island, Calf Island and Shore Island in the distance. It also has a playground, concession stand, and small park to wander around in, grill, enjoy a picnic etc.
Lunch: Bartaco
If you decide to skip lunch at the beach, a great place, still on the water for lunch is Bartaco. However, this restaurant is not located on the Long Island Sound, but on the Byram River. Bartaco is technically located in Portchester, NY (across from Byram). Churros, tacos, and margaritas are served all day long and if you have a boat you can anchor it on their dock and go in for lunch. It’s a very popular spot, especially on a beautiful sunny day, so make sure to book in advance if you don’t want to wait for an hour or more. Note: The music can get loud so if that’s not your vibe, safer to stick to the concession stands and grills at Byram Shore Park.
Afternoon: Walk Byram Shore Road
Ok, on some weekends, particularly long weekends like Memorial Day or 4th of July, the private community of Byram Shore Road (specifically Hawthorne Association), will hire a security guard to scare away people from walking down the road by saying it’s “PRIVATE.” Aside from those weekends, you’re able to walk down to Hawthorne Beach and back. As you walk, there are signs everywhere that say the road is private, but it actually is a public road. It’s just a scare tactic used to keep people away. Here you’ll find some of the most beautiful homes in all of Greenwich. I love just walking down and admiring the homes. I would be respectful and just not be too loud as you stroll down the street. You’ll usually see another person or two walking at the same time as you. Word of caution: Do not walk onto their beach. That’s one thing I never do as that truly is a private beach exclusively for the association. There are limits!
Afternoon: Griffith E Harris Golf Course
Whether you just want to practice some swings at the driving range or want to play 18 holes, the Griffith E Harris is the only non-private golf course in Greenwich. Because of that, tee times get swept up early, and members and residents do get priority. If you plan on playing 18, make sure to reserve far in advance. Early morning times are best if it’s the summer. The driving range on the other hand is just a walk up so doesn’t require any planning.
Afternoon: Stop by Augustine Farm
Before being home to lavish mansions and luxury retailers, Greenwich started off as an agricultural landscape. Where each mansion now stands, there used to be farms and acres of land. Sadly, little remains of Greenwich’s agricultural history today, aside from the mansion’s architecture and a couple of head nods here and there in the form of names like Mead. One of the only ways Greenwich’s agricultural history still survives is through Augustine Farm. Augustine Farm is the last working farm in all of Greenwich, CT. This 10-acre farm, run by the Augustine family, has been around for over 65+ years. On your way back from the Griffith, stop by a pick up some fresh vegetables, eggs from their hens, honey from their beehives, or flowers. In the winter, they sell Christmas trees and in the summer the trip to backcountry is worth it for their sweet summer corn.
– Day 6 –
Morning: Day trip to Rowayton
Ok, Greenwich, CT is a lovely place to live. And if this itinerary hasn’t convinced you of it, I don’t know what will. But there is more to see and visit beyond the boroughs of Greenwich, CT. Greenwich is the gateway to New England, so it’s imperative to visit a few other jewels in the area. One of my favorite spots to visit for lunch is Rowayton Seafood. It’s one of the few places directly on the water, specifically the Five Mile River,(aside from the Delamar) in the area. You can either come by boat and dock at one of their moorings or the dock itself (reservations required in advance). From there you can either eat on the boat or at the restaurant. Or two, drive to the restaurant. Of course the go to food here is the seafood. My personal favorite is the Lobster Cobb salad.
There’s not much more to do in Rowayton as the village is fairly small. But you can walk down the rest of the road by the Five Mile River, or bring your kayak and pot it in at one point to enjoy the views and homes from the water.
Afternoon: Day trip to Westport
In the afternoon, I recommend you go to my second favorite village in Fairfield County (after Greenwich) – Westport! If Westport weren’t an extra 20-30 minute commute from NYC I would’ve considered it as a place to live. The main village is bumping with plenty of popular and boutique shops and restaurants, similar to Greenwich Avenue. Westport has plenty of events year round including one of my favorites – Octoberfest. And if you’re interested in a one-of-a-kind CT experience, you can book a public or private oyster tour at Hummock Island. Located in Sherwood Millpond, the island is small with just a porch and small platform where people can enjoy a drink and some oyster shucking and tastings.
– A Week or More in Greenwich, CT: 2 – 6 Day Itinerary Map –
– Where & What to Eat in Greenwich, CT –
Dining around Greenwich, CT is a scene. From nationally acclaimed establishments to cool, budget-friendly hangouts, there’s something for every taste in all 5 of Greenwich, CT’s neighborhoods. Here are 32 of my favorite restaurants, bakeries, bars, pubs diners and delis where you can eat in Greenwich, CT according to me, Sveva–a local.
– How to Get Around Greenwich, CT –
While having your own car is by far the best way to get around Greenwich, CT. I can’t lie, our public transportation system is quite robust. The Metro North Railroad stops in the center of all 5 of the main villages: Port Chester for Byram, Greenwich, Cos Cob, Riverside, and Old Greenwich. The train stations are walkable to most of the restaurants, parks, and beaches. So if you wanted to get around just by train, you could. Exceptions are made for anything in backcountry, like the Greenwich Polo Club, Griffith Golf Course, and Augustin Farm. Those will require uber and lyft, which we have plenty of in the area.
If you’re big into cycling, I’ve cycled from Byram to Old Greenwich Tod’s Point Beach more times then I can count. Cycling all of Greenwich is quite easy as long as you stick to the cost. Backcountry gets extremely hilly and far.
