Old Greenwich, Connecticut: What to Bring, what to Pack, and what to Wear


Select the month that you will be traveling from the table below to view the packing list:

JanuaryFebruaryMarchApril
MayJuneJulyAugust
SeptemberOctoberNovemberDecember

What Old Greenwich is like to visit throughout the year:

January

When traveling to Old Greenwich in January, it is important to dress warmly and in layers. The temperatures can drop quite low, especially at night, so be sure to bring a heavy coat, gloves, and a hat. A good pair of waterproof boots is also essential, as there may be snow and ice on the ground. I recommend bringing a scarf as well, as it can provide extra warmth and can easily be removed if the temperature rises during the day. In terms of what to wear, I suggest packing comfortable and practical clothing that can easily be layered. Sweaters, long-sleeved shirts, and pants are a must. Avoid packing any bulky or heavy items, as they can take up valuable space in your luggage. It is also a good idea to bring a small backpack or day bag for exploring the town, as well as a reusable water bottle to stay hydrated. Lastly, don’t forget to bring a camera to capture the beautiful winter scenery and a map to navigate the charming streets of Old Greenwich. With the right clothing and essentials, you’ll be able to fully enjoy your January trip to this picturesque New England town.

January is a wonderful time to visit Old Greenwich, a charming coastal town just a short train ride away from New York City. The winter season brings a peaceful and cozy atmosphere to this quaint village, making it the perfect destination for a relaxing getaway. One of the must-do activities in January is taking a stroll along the waterfront and admiring the picturesque views of the Long Island Sound. The crisp air and serene surroundings make for a delightful walk, and you may even spot some winter wildlife along the way. When in Old Greenwich, be sure to visit the Bruce Museum, a hidden gem that showcases a diverse collection of art and science exhibits. In January, the museum hosts its annual Winter Lecture Series, featuring renowned speakers discussing a variety of topics from art and history to science and nature. This is a fantastic way to spend a cold winter afternoon, gaining knowledge and inspiration while staying warm indoors. And after the lecture, grab a cup of hot cocoa from one of the local cafes and continue exploring the charming streets of Old Greenwich.

February

As you pack for your February trip to Old Greenwich, keep in mind that the weather can be quite unpredictable. It’s best to dress in layers so you can adjust to the changing temperatures throughout the day. A warm winter coat, scarf, and gloves are essential for exploring the charming streets of Old Greenwich. Don’t forget to pack a sturdy pair of waterproof boots, as the sidewalks can be slippery after a snowfall. And don’t be afraid to add a pop of color to your outfit with a bright hat or scarf – it will make for some great photos against the snowy backdrop. When visiting Old Greenwich in February, it’s important to also consider the activities you have planned. If you’re going to be doing some outdoor activities, such as hiking or skiing, make sure to pack appropriate gear like a warm hat, waterproof pants, and a pair of comfortable, insulated boots. For a more relaxed day, opt for some cozy sweaters, jeans, and comfortable shoes. And don’t forget to bring a small backpack to carry essentials like water, snacks, and a camera to capture the beautiful winter scenery. With the right clothing and gear, you’ll be able to fully enjoy all that Old Greenwich has to offer in February.

February is a wonderful time to visit Old Greenwich, Connecticut. This charming seaside village offers a variety of activities for travelers to enjoy during the colder months. One must-see attraction is the Bruce Museum, which features a diverse collection of art and natural history exhibits. Take a stroll through the museum’s winter garden and admire the beautiful sculptures and plantings. For outdoor enthusiasts, the Greenwich Point Park offers stunning views of the Long Island Sound and is perfect for a brisk winter hike. Don’t forget to stop by the historic lighthouse, built in 1827, for a unique photo opportunity. Foodies will also delight in the culinary scene of Old Greenwich. February is the perfect time to indulge in some hearty New England cuisine. Be sure to try the local seafood, especially the famous Connecticut lobster roll, at one of the many cozy restaurants in the village. For a taste of history, visit the Putnam Cottage, where George Washington stayed during the Revolutionary War. The cottage now serves as a charming museum and tea room, offering a delightful afternoon activity. So bundle up and come experience the quaint charm of Old Greenwich in February!

March

March is a lovely time to visit the charming town of Old Greenwich. As the winter snow begins to melt away, the town comes alive with the sights and sounds of spring. When it comes to dressing for this time of year, layering is key. The weather can be unpredictable, with chilly mornings and warm afternoons, so it’s important to be prepared. I recommend bringing a light jacket or sweater, a scarf, and a comfortable pair of walking shoes. This way, you can easily adjust your outfit to the changing temperatures and be ready for any adventure that comes your way. As you explore the quaint streets of Old Greenwich, you’ll want to blend in with the locals and dress comfortably for the day’s activities. I suggest wearing jeans or casual pants paired with a light sweater or long-sleeved shirt. This will keep you warm and stylish as you stroll through the town’s charming shops and cafes. Don’t forget to bring a small backpack or tote bag to carry any essentials such as a water bottle, sunscreen, and a map. And of course, a camera is a must to capture the picturesque beauty of Old Greenwich. With these tips, you’ll be dressed and prepared for an unforgettable visit to this delightful town.

Welcome to Old Greenwich, a charming coastal town in Connecticut. While many visitors flock to this area during the summer months, March offers a unique and quieter experience. One of the best ways to start your day in Old Greenwich is with a walk along the picturesque Greenwich Point Beach. This stretch of sandy shoreline offers stunning views of the Long Island Sound and the chance to spot some local wildlife. Be sure to bundle up, as the sea breeze can be chilly in March. After your morning stroll, head over to the Greenwich Avenue shopping district for some retail therapy. This charming street is lined with boutique shops, cafes, and restaurants, making it the perfect place to spend a leisurely afternoon. Don’t miss the Greenwich Historical Society, where you can learn about the town’s rich history and see exhibits featuring local artists. And if you’re feeling adventurous, take a short drive to the nearby Audubon Center for a scenic hike through the woodlands and wetlands of the Greenwich Peninsula. With its mix of natural beauty and small-town charm, Old Greenwich is the perfect destination for a March getaway.

April

As you plan your trip to Old Greenwich in April, it’s important to consider the weather and pack accordingly. While the temperatures can still be cool, the springtime brings blooming flowers and a sense of renewal to this charming New England town. I recommend dressing in layers, with a light jacket or sweater for the cooler mornings and evenings, and a t-shirt or light blouse for the warmer afternoons. Don’t forget to pack a waterproof jacket or umbrella, as April can bring some rain showers. When exploring Old Greenwich, comfort is key. Be sure to bring a comfortable pair of walking shoes for strolling through the town’s picturesque streets and parks. As for accessories, a scarf or hat can add a touch of style while also keeping you warm. And of course, don’t forget a camera to capture the beauty of the town’s historic buildings and scenic coastline. As always, be respectful of local customs and dress modestly when visiting churches or other religious sites. With these tips in mind, you’ll be well-prepared for a delightful April visit to Old Greenwich.

Welcome to Old Greenwich, a charming coastal town in Connecticut. April is a wonderful time to visit this quaint community, as the weather starts to warm up and the flowers begin to bloom. As a seasoned traveler, I highly recommend taking a stroll along the picturesque Greenwich Point Beach, where you can enjoy views of the Long Island Sound and spot some local wildlife. If you’re feeling adventurous, you can even rent a kayak or paddleboard and explore the waters on your own. For history buffs, I suggest checking out the Bush-Holley House, a historic home turned museum that offers a glimpse into the town’s past as an artist colony. You can also visit the Mead Visitor Center, where you can learn about the town’s maritime history and explore artifacts from the area’s first European settlers. April is also the perfect time to attend the Daffodil Festival, a yearly event that celebrates the blooming of thousands of daffodils throughout the town. With its charming atmosphere and abundance of activities, Old Greenwich is the perfect destination for an April getaway.

May

When visiting Old Greenwich in May, it’s important to pack for a variety of weather conditions. The springtime in Connecticut can be unpredictable, with warm sunny days followed by cool evenings. I always recommend dressing in layers, so you can easily adjust to the changing temperatures. A light jacket or raincoat is essential, as well as comfortable walking shoes for exploring the charming streets and parks of Old Greenwich. In terms of clothing, I find that a mix of casual and slightly dressy attire works well in this area. For daytime activities, opt for comfortable yet stylish outfits such as jeans, t-shirts, and light sweaters. In the evenings, you may want to dress up a bit for dinner at one of the town’s quaint restaurants or attending a local event. Don’t forget to bring a swimsuit and beach cover-up if you plan on taking a dip in the Long Island Sound or lounging on the nearby beaches. And of course, don’t forget your camera to capture the beautiful scenery and historic buildings of Old Greenwich. Happy travels!

May is a delightful time to visit Old Greenwich, nestled along the scenic Connecticut coast. As the weather warms up and the trees start to bloom, this charming neighborhood comes to life with a variety of activities for visitors to enjoy. One must-do experience is taking a leisurely stroll along the picturesque Greenwich Point Park, with its sandy beaches, walking trails, and stunning views of the Long Island Sound. It’s the perfect place to soak up some sunshine and snap some postcard-worthy photos. For history buffs, a visit to the Bush-Holley House is a must. This 18th-century home turned museum offers a fascinating glimpse into the past of Old Greenwich, with its well-preserved rooms and artifacts. In May, the house also hosts a variety of events, such as traditional craft demonstrations and musical performances, adding an extra layer of charm to the experience. And don’t miss out on exploring the quaint downtown area, with its boutique shops, cozy cafes, and delicious seafood restaurants. May is the perfect time to visit Old Greenwich and discover all it has to offer.

June

When planning a trip to Old Greenwich in June, it’s important to keep in mind the warm and sunny weather. The average temperature during this time is around 80 degrees Fahrenheit, so packing lightweight and breathable clothing is a must. I recommend bringing a mix of shorts, t-shirts, and sundresses for daytime activities, and a light jacket or sweater for cooler evenings. Don’t forget to pack comfortable walking shoes as well, as Old Greenwich is a charming small town with plenty of opportunities for strolling around. Another essential item to pack for a June visit to Old Greenwich is sunscreen. With the sun shining bright and the coastal breeze, it’s easy to underestimate the strength of the sun’s rays. Be sure to bring a hat and sunglasses as well to protect yourself from the intense sun. As for accessories, a small crossbody bag or backpack is perfect for carrying essentials while exploring the town. And don’t forget a reusable water bottle to stay hydrated while on the go. With the right clothing and gear, you’ll be well-prepared for a delightful summer visit to Old Greenwich.

Welcome to Old Greenwich, a charming and historic town on the coast of Connecticut. As the summer season begins in June, this quaint town comes alive with a variety of activities for travelers to enjoy. One of the top attractions is the Greenwich Point Park, where you can soak up the sun on the sandy beach, take a dip in the Long Island Sound, or go for a scenic hike on one of the many trails. Don’t forget to pack a picnic and enjoy a relaxing afternoon surrounded by nature. For a taste of local culture, be sure to visit the Greenwich Historical Society. This museum showcases the town’s rich history through exhibits and interactive programs. In June, the Historical Society also hosts their annual Antiquarius event, featuring a variety of antiques and fine arts for sale. And for those looking to indulge in some retail therapy, the charming streets of Old Greenwich are lined with unique shops, perfect for finding a special souvenir or gift. No matter your interests, Old Greenwich in June offers something for everyone to enjoy.

July

When visiting the charming town of Old Greenwich in July, it’s important to dress for both comfort and style. The weather in this quaint New England town can be quite warm, so lightweight and breathable clothing is a must. Opt for loose-fitting cotton tops and shorts or skirts for a casual and relaxed look. Don’t forget to pack a light jacket or sweater for the cooler evenings, as well as a hat and sunglasses for protection from the sun. In addition to clothing, it’s important to bring comfortable walking shoes when exploring Old Greenwich. With its picturesque streets lined with boutiques, cafes, and historic homes, this town is best explored on foot. A small crossbody bag is also recommended to carry essentials such as a water bottle, sunscreen, and a camera to capture the beautiful scenery. And of course, don’t forget to bring a sense of adventure and an open mind to fully experience the charm and beauty of Old Greenwich.

July is a fantastic time to visit Old Greenwich, a charming coastal town in Connecticut. As the summer heats up, the town comes alive with festivals, outdoor activities, and beautiful views of the Long Island Sound. One of the must-do activities in July is to take a stroll along the Old Greenwich Beach. With its soft sands, gentle waves, and stunning sunsets, it’s the perfect spot to relax and soak up some sun. For those feeling more adventurous, I recommend renting a kayak or stand-up paddleboard and exploring the calm waters of the Sound. Another highlight of July in Old Greenwich is the annual Old Greenwich Independence Day Celebration. This event, held on July 4th, is a true celebration of American pride and community spirit. The day starts with a parade through the town, featuring local organizations, marching bands, and creative floats. After the parade, head to Binney Park for a picnic and enjoy live music, food trucks, and games for the whole family. As the sun sets, make sure to stay for the spectacular fireworks display over the Sound. It’s a day filled with small-town charm and patriotic spirit that should not be missed.

August

When visiting Old Greenwich in the month of August, it’s important to dress for the warm and humid weather. Lightweight, breathable clothing is key to staying comfortable while exploring this charming neighborhood. Opt for cotton or linen fabrics in light colors to help beat the heat. A sun hat and sunglasses are also essential items to protect yourself from the strong summer sun. It’s also important to bring comfortable walking shoes as Old Greenwich is best explored on foot. The cobblestone streets and sidewalks can be uneven, so sturdy shoes will help you navigate the area with ease. Additionally, don’t forget to pack a light jacket or sweater for cooler evenings, as well as an umbrella in case of afternoon showers. And of course, don’t forget your camera to capture all the picturesque moments in this quaint New England town. Happy travels!

When visiting Old Greenwich in the month of August, there are plenty of activities to keep you entertained. First and foremost, take a stroll along the picturesque coastline and enjoy the stunning views of Long Island Sound. The water is warm and inviting, making it the perfect spot for a swim or a relaxing beach day. For a more active experience, rent a kayak or stand-up paddleboard and explore the coves and inlets of the shoreline. And don’t forget to pack a picnic and enjoy a leisurely lunch on the beach. If you’re looking for a break from the beach, head to the charming downtown area of Old Greenwich. Here you’ll find a variety of boutique shops and local restaurants to explore. Be sure to check out the weekly farmers market for fresh produce and artisanal goods. For history buffs, a visit to the Bush-Holley House, a historic landmark and former home of American Impressionist artists, is a must-see. And for a bit of outdoor fun, take a hike through the nearby Mianus River Park and admire the lush greenery and serene atmosphere. No matter your interests, Old Greenwich in August has something for everyone to enjoy.

September

When visiting Old Greenwich in September, it’s important to dress in layers. The weather can be quite unpredictable during this time, with warm days and cool evenings. I recommend bringing a light jacket or sweater that you can easily take on and off as needed. It’s also a good idea to bring comfortable walking shoes as you’ll want to explore the charming streets and parks of this historic neighborhood. As for what to wear, I suggest sticking to comfortable, casual attire. Old Greenwich has a relaxed and laid-back atmosphere, so leave the fancy clothes at home. Opt for breathable fabrics such as cotton or linen to stay cool during the warmer days. And remember to bring a hat and sunglasses to protect yourself from the sun. Lastly, don’t forget to pack a reusable water bottle and sunscreen as you’ll likely be spending a lot of time outdoors. With these tips in mind, you’ll be well-prepared to enjoy all that Old Greenwich has to offer in September.

Welcome to Old Greenwich in September, fellow travelers! As the summer crowds disperse and the crisp autumn air sets in, this charming seaside town takes on a whole new vibe. One of my favorite activities during this time is to take a stroll along the picturesque waterfront. The leaves may be changing, but the views of the Long Island Sound remain just as stunning. Stop by the local market to pick up some fresh seafood and have a picnic by the water, or rent a kayak and explore the coastline from a different perspective. No matter what you choose, you’ll be sure to experience the peaceful beauty of Old Greenwich in the fall. For history buffs, September is the perfect time to delve into the rich past of this quaint New England town. Take a guided walking tour through the historic district and learn about the town’s role in the American Revolution. Visit the Bush-Holley House, a museum that showcases the town’s influential artistic and literary history. And don’t miss the annual Old Greenwich Heritage Day event, where you can immerse yourself in the town’s culture and traditions. With the pleasant weather and smaller crowds, September is the ideal time to discover the hidden gems and fascinating stories of Old Greenwich. Happy travels!

October

When traveling to Old Greenwich in October, it’s important to dress in layers to prepare for the unpredictable weather. The autumn season brings cooler temperatures and occasional rain showers, so I recommend packing a lightweight rain jacket and a few sweaters or jackets that can easily be removed if the sun decides to make an appearance. Comfortable walking shoes are a must, as Old Greenwich is a pedestrian-friendly town with plenty of charming shops and cafes to explore. As for what to wear, I suggest opting for a comfortable yet stylish outfit. Locals in Old Greenwich tend to dress casually, but it’s always nice to add a touch of elegance with a scarf or a nice pair of shoes. And don’t forget to bring a camera! The beautiful foliage and scenic waterfront make for some stunning photo opportunities. Lastly, be sure to pack a reusable water bottle and a small snack to keep you fueled throughout the day. With these tips, you’ll be well-prepared for a wonderful autumn adventure in Old Greenwich.

October is a wonderful time to visit Old Greenwich, a charming coastal town in Connecticut. As the leaves begin to change and the air turns crisp, this idyllic New England community comes alive with seasonal activities and attractions. One of the best things to do in Old Greenwich during this time is to take a stroll along the picturesque Greenwich Point Park. The park offers stunning views of the Long Island Sound and is the perfect spot for a leisurely walk or bike ride. In addition, October is prime time for apple picking, and the nearby Stamford Museum and Nature Center offers a delightful orchard where visitors can pick their own apples and enjoy other fall festivities. For a taste of local culture, be sure to check out the annual Old Greenwich Art Show, featuring works from talented artists in the area. With its charming atmosphere and endless activities, Old Greenwich is the perfect fall destination for any traveler.

November

November is a wonderful time to visit Old Greenwich, with mild temperatures and beautiful autumn foliage. When it comes to dressing for this charming New England town, it’s important to be prepared for both indoor and outdoor activities. A waterproof jacket or coat is a must, as well as layers such as sweaters and scarves. The weather can be unpredictable, so it’s always a good idea to bring an umbrella. Comfortable walking shoes are also essential, as Old Greenwich is best explored on foot. As for what to wear, I recommend sticking to classic, casual and comfortable attire. This is a laid-back town, so leave your fancy clothes at home. Opt for jeans or khakis paired with a cozy sweater or flannel shirt. Locals often sport stylish rain boots, so don’t be afraid to add a bit of flair to your outfit. And don’t forget a warm hat and gloves to keep you toasty during those brisk walks along the shore. Lastly, be sure to bring a camera to capture the picturesque streets, historic buildings, and stunning views of Long Island Sound. With these tips in mind, you’ll be ready to experience all that Old Greenwich has to offer in the cozy month of November.

As the brisk autumn air sets in, Old Greenwich is the perfect destination for a cozy November getaway. Start your day with a leisurely stroll along the charming streets lined with historic homes and quaint shops. Be sure to stop by the local farmer’s market, where you can sample fresh produce and homemade goods from the surrounding farms. After working up an appetite, head to one of the many cozy cafes for a hot cup of coffee and a slice of homemade pie. November is also the perfect time to explore the natural beauty of Old Greenwich. Take a scenic drive along the coast and admire the stunning fall foliage. For a more active adventure, rent a bike and ride along the scenic trails of Greenwich Point Park. And don’t forget to visit the Audubon Center, where you can spot a variety of migratory birds passing through the area. As the day comes to a close, cozy up by the fire at one of the charming bed and breakfasts and enjoy a glass of local wine. November in Old Greenwich truly offers something for every traveler.

December

As you embark on your journey to Old Greenwich in December, it’s important to pack accordingly for the chilly weather. The key to staying warm and comfortable is layering. Start with a base layer made of moisture-wicking material, such as wool or synthetic fabrics. This will keep you dry and insulated as you explore the charming streets of Old Greenwich. On top of that, add a sweater or fleece for extra warmth. A waterproof and windproof outer layer, such as a parka or rain jacket, is a must-have for any outdoor activities. Don’t forget to pack a warm hat, scarf, and gloves to protect your head, neck, and hands from the cold. And of course, a sturdy pair of waterproof boots will keep your feet dry and comfortable as you navigate the cobblestone streets and potentially snowy sidewalks. As for what to wear, Old Greenwich is known for its quaint and picturesque atmosphere, so it’s always a good idea to dress in layers that are both functional and stylish. Opt for dark, neutral colors that will easily mix and match, and choose pieces that can be dressed up or down. A pair of jeans or leggings paired with a warm sweater and a stylish coat will keep you cozy and fashionable. And when visiting any churches or religious sites, it’s important to dress modestly and cover your shoulders and knees. Lastly, don’t forget to bring a small crossbody bag to carry your essentials, as well as a reusable water bottle to stay hydrated during your winter adventures in Old Greenwich.

When visiting Old Greenwich in December, there are a plethora of festive activities to partake in. One must-see attraction is the annual Christmas Tree Lighting Ceremony in Binney Park. This charming event brings the community together with carol singing, hot cocoa, and of course, the lighting of the town’s Christmas tree. It’s a magical experience that captures the holiday spirit perfectly. For a more low-key activity, take a stroll through the quaint streets of Old Greenwich and admire the beautifully decorated homes. Many residents go all out with festive lights and decorations, making for a picturesque winter wonderland. Stop by the local shops and boutiques to find unique gifts for your loved ones back home. And don’t forget to indulge in some delicious holiday treats at the various bakeries and cafes scattered throughout the town. Old Greenwich truly comes alive during the month of December, making it the perfect destination for a cozy and festive getaway.

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