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The 203's Town Guide To New Canaan Connecticut

The 203's Town Guide To New Canaan Connecticut


To help you explore some of our favorite local areas, we’re working on creating ‘Town Guides’ to several of our favorite Connecticut towns & neighborhoods! Whether you’re new to the area, you’ve lived here for years, or you’re simply looking to plan a (covid safe) trip to explore some new spots around the state, our #203TownGuides will give you the inside scoop and everything you need to know to get started!

The 203's Town Guide To New Canaan CT

Together with our friend and real estate expert, Cindy Raney ( @cindyraneyrealtor) we are so excited to bring you our next #203TownGuide! This month, we’re taking you slightly off of the CT Shoreline to the picturesque town of New Canaan, Connecticut. Together with Cindy, we spent a few afternoons exploring the neighborhoods of N.C., checking out the parks, sampling margs in Downtown, and talking to the locals :)  

Of course, you can’t get the scoop on a town without turning to the locals! We’ve teamed up with a few of our favorite local ladies (and New Canaan gurus) Megan from @CampByMama and Ruth from @Stylinitbyruth to bring you the insider's advice on New Canaan! With their help, we’ve rounded up a list of epic spots to check out on your next trip to New Canaan! 

Our 'Tour Guides': @CampByMama and @Stylinitbyruth

Our Town Guide to New Canaan, Connecticut: 

Town Guide To New Canaan The 203

Nestled in the southwest corner of Connecticut, the picturesque town of New Canaan has a small town vibe with a big personality. Located in Fairfield County on the Fivemile River, this fairytale community borders New York State and is a quick commute to manhattan. We love New Canaan for it’s deep rooted town pride, tight knit community and its iconic town center that is SO quaint…. that it seems as if it was pulled directly out of a story book. 

You’ll fall in love with New Canaan for its charm, but you’ll keep coming back for the bustling restaurant scene, great shopping and feel good vibe. The thriving downtown is filled with trendy boutiques, top notch restaurants and some of the best spots for outdoor happy hours!  

This Connecticut community has endless activities to be enjoyed by residents and visitors alike. Overflowing with pristine parks, cultural exhibits and recreational areas, New Canaan will keep just about anyone busy! 

Outdoor Fun: 

Outdoor Activities in New Canaan CT

PARKS: New Canaan is filled with pristine parks and hidden gems that you will not want to miss. For trail maps, park details, hours and parking information click HERE. Below are a few of our faves! 

Mead Park: This spot comes highly recommended by our friend and local expert, Megan (from @CampByMama ). Her and her fam love Mead Park for the endless activities and top of the line facilities including a baseball field and playground! According to her, Mead Park is a huge draw in town.. And her PRO TIP-- don’t miss the Apple Cart (YUM). 

Waveny Park: This place is a locally loved gem amongst locals. This legendary park draws locals and visitors of all ages, because there is something for everyone to enjoy! With approximately 3.5 miles of jogging/walking trails, endless sporting fields (soccer, baseball, & softball fields), a beautiful picnic area, Platform Tennis Courts, a Swimming Facility, artificial turf field, a Water Tower… this park will NOT disappoint! Waveny Park also contains the PowerHouse Performing Arts Center, The Carriage Barn, Spencer's Run Dog Park, Lapham Community Center and The Waveney Lodge and Platform Tennis Courts. Waveny typically hosts town wide events such as a music concert series and the 4th of july fireworks--- and locals are hoping that these activities will resume soon! 

Irwin Park: The 36 acre park has newly opened jogging/walking trails for your enjoyment. We loved visiting earlier this month for the breathtaking display of daffodils that take over the sprawling field. 

New Canaan Mounted Troup: This amazing organization is near and dear to Ruth (from @stylinitbyruth) and her daughter’s hearts! Ruth explains “New Canaan Mounted Troop which the most incredible horsemanship program for children. You walk in the barn doors loving horses and come out with so much more! “ We loved hearing all about this hidden gem and can’t wait to check it out! Ruth volunteers for Super Troopers, which is equine assisted activities for individuals with special needs.

New Canaan Nature Center: This hands-on Nature Center has 40 acres of land to explore! Complete with two miles of walking tails through meadows and woodlands, two ponds and an observation tower. 


Art's & Culture: 

Arts and Culture in New Canaan Connecticut

The Glass House: This unique piece of art draws crowds from all over the country. In addition to the ‘glass house’ it features a permanent collection of 20th-century painting and sculpture, along with temporary exhibitions. Tours of the site are available in April through November and advance reservations are recommended.


Grace Farms: This 80-acre public space is an extremely unique place. Open to the public, Grace Farms is a non-profit center dedicated to initiatives concerning nature, the arts, community, justice and faith. Grace Farms does not mess around--- The facility is equipped with a 700-seater amphitheater, a tea pavilion, a library, a commons space with an excellent organic cafe and a sunken court for performing arts and recreation.Spend the afternoon roaming around the immaculate grounds of the property-- explore the walking trails and experience the contemporary art installations by the likes of Teresita Fernández, Olafur Eliasson and Thomas Demand. ** Currently closed due to COVID. Check their website for updates and opening schedule. 

Silvermine Arts Center: A beautiful oasis that offers a variety of art classes and gorgeous exhibits for a large range of ages and skill sets. The mission of Silvermine Arts Center is “to cultivate and encourage growth through the arts; to promote and showcase artists; and to provide arts education opportunities for the greater community”. 

The Carriage Barn Arts Center: This 19th century stone barn, located in Waverly Park, has been transformed and refurbished into a gorgeous gallery and center for the performing arts. Each season The Center offers a plethora of unique events and exhibits and the space is open to all members of the surrounding community and anyone who is interested in the arts.


Shopping Downtown New Canaan CT

New Canaan does not fall short in the shopping category, that’s for sure. The bustling town center has a vast variety of locally owned boutiques with unique and trendy items for every age range. 

Elm street is home to the ‘heart’ of downtown and is not to be missed-- we suggest starting on Elm and wandering the surrounding streets. Don’t be shy! Take the time to walk up and down the small alleyways- you will find some hidden gems and the cutest spots when you explore all the nooks and crannies. 

In downtown New Canaan you can find gifts and treasures for all ages and price ranges. 

Looking for 203 goodies? (HECKKKY YEAA!!) Head to our fave-- Groove! It’s located directly on Elm and has tons of 203 gear! 


Where To Stay? 

Roger Sherman Inn New Canaan Connecticut

The Roger Sherman Inn: This iconic Connecticut gem is a beloved piece of New Canaan history and a stunning location to host a special event. Located on a 250 year old property, the Inn will bring you quintessential New England charm with all the amenities of a luxury venue. Completely renovated in 2019 this gorgeous property is equipped with 6 luxe dining rooms, beautiful outdoor seating areas, 15 luxury guest rooms and customer service that will not disappoint. We grew up going to the Roger Sherman Inn at Christmas time to enjoy the unbelievably holiday decor. 


The Food Scene: 

Whether you're looking for a girls night out, a bite with the kids, the perfect spot for a special date night or a quick (yet delish) classic deli sandwich-- New Canaan has you covered! The options are endless, and we're only naming a FEW of our faves! 

Breakfast, Brunch and laidback lunch…

Lunch in New Canaan Connecticut  

UCBC: If bagels are your jam, UCBC is your spot. This long time fave for NC locals serves up fresh bagels, delicious breakfast and casual lunch in the heart of downtown. We love the family friendly vibe and the laid back atmosphere at UCBC.  

Rosie’s: This New Canaan staple is not to be missed. At Rosie’s, they claim to serve” good food, good coffee, and good wine” but in reality their food, coffee and wine is nothing short of exceptional. Rosie’s is a community driven cafe dedicated to serving the community delicious, healthy & mindful eats that will blow your taste buds away!

Silvermine Market: Located off the beaten path, Silvermine Market is a locally loved gem with delicious food and a feel good ambiance. Whether you come here every weekend, or you’ve never been--- at Silvermine Market you will feel like a regular. Don't miss this pizza!

Tony’s deli: A perfect option for great sandwiches to go. 

Greenology: This plant based kitchen is a vegans dream come true. But, you definitely don't have to be vegan to LOVE their food (trust us on this one!!). Greenology is a community driven cafe with a passion for serving healthy and sustainable food. 

Zumbach's Gourmet Coffee: We are allllll about finding a great locally owned coffee shop, and this place did not disappoint. You will be able to smell this place out… literally! We love that they roast their own beans and that they are committed to the NC community! 

Girls Night Out OR Fun Night with your Besties! 

Food Scene In New Canaan Connecticut

The Back End: Located directly behind Uncorked, this spot is slightly off the beaten track-- making it the best hidden gem on Elm street. Hip atmosphere, vibrant ambiance, great music, epic outdoor patio and margs that are even more delicious than they look (shocking, we know!!). If you’re looking for a fun spot for outdoor drinks with your besties, The Back End is not to be missed. 

Elm: Great food, excellent ambiance and perfect for families. We love their fixed price afternoon tea for a special occasion! Thanks for the suggestion @Zaczac.mathias :) 

Tequila Mockingbird: Located in the heart of downtown New Canaan, Tequila Mockingbird serves fresh, authentic Mexican cuisine in a friendly, upbeat and eclectic environment.

Uncorked: A bustling atmosphere with a neighborhood vibe. This modern day ‘speakeasy’ has exactly the ambiance that we look for in a great hang out. We love that from the front Uncorked doesn't look like anything special, but when you know what’s inside, you will come back again and again. When you wander down the side alley and enter from the back entrance you are instantly transported to an intimate, vibey bar with a hip and chick atmosphere. The food and drinks at Uncorked are unbelievable and the staff makes you feel like family. 

White Buffalo: Off the beaten path and totally our vibe. This laid back casual pub has great food, fun vibes, and cold beers on tap. This place came highly recommended by local guru, @campByMama --and we are so glad she suggested it! (Pro tip: Check their live music schedule! They have outdoor music on the patio and it is not to be missed!) 

Date Night:

Sole: From the moment you enter Sole, you are greeted with a warm sense of exceptional hospitality. The food is cooked to perfection and the ambiance… is just right. Pro Tip: Sit outside

Farmer’s Table: They’ve been crushing the ‘farm to table’ game, long before ‘farm-to-table’ was a trendy term. At Farmer’s Table every plate is made to order  using the freshest ingredients that are reliably and responsibly sourced-- and trust us, you can taste the difference.  

Spiga: Locally sourced dishes inspired by classic Italian fare. At Spiga, they pride themselves on their handmade pastas and brick oven pizzas with a sharp attention to detail.

Cava Wine Bar: When you visit Cava Wine Bar, you will be transported to a subterranean enclave. At Cava, they boast a modern approach to Italian cuisine with local ingredients, fresh seasonal menus and a family principle of hospitality. 

Locali Pizza Bar: We love Lacali for their stellar food, laid back atmosphere and outdoor seating. Locali has great vegan options and the food will blow you away! 

Sweet tooth! 

Desert in New Canaan CT

Gelaticcimo: Authentic Italian gelato made from scratch… need we say more? We love that Gelatissimo offers ever changing seasonal flavors. On any given day they offer an average of 18-22 flavors… So, your biggest challenge will be which one to pick! In addition to gelato, they also offer gelato cakes, crepes filled with nutella and gelato, and a coffee bar that will rock your world. 

Patisserie Salzburg: Patisserie Salzburg is an upscale European-style cafe located on Elm Street. They offer fresh, authentic food and baked goods in a warm, inviting environment. Excellent selection of pastries, cookies and cakes. 

Waffle Cabin: Originated on the slopes of Vermont, this waffle cabin meets food truck serves up delicious, freshly baked belgian waffles, ice cream and more! They are often seen cruising around New Canaan (but will trek all over Fairfield county and take appointments for private parties!) 


Self Care, Anyone? 

Calme New Canaan The 203's Town Guide to NC

Let's just say, if you are looking for an extremely special treat, head to CalmeThis is @CampByMama ‘s go to for a unique and relaxing experience that you can't get anywhere else... and we were stoked for the recommendation! A female owned, local bizz serving up all things self care-- this spot will make you feel like a damn queen. Their infrared Sauna brings relaxation, rejuvenation, health, and healing to the heart of New Canaan!

Looking To Relocate To New Canaan?

The 203 Cindy Raney & Co

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