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The 203's Town Guide To Westport Connecticut

The 203's Town Guide To Westport 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!

For our second #203TownGuide, we decided to give you guys the inside scoop on the town we grew up in — Westport CT. To help us make sure we covered (almost) all of Westport’s gems, we couldn’t think of a more perfect person to help us with the task. For our Town Guide To Westport, we partnered with our friend and local real estate expert, Cindy Raney, to round up a list of our favorite hometown spots that make this town such a special place.

Before the pandemic, one of Cindy’s favorite things to do with clients moving to the area from out of state was to drive them around, point out her go-to local spots and give them an authentic local tour of their new ‘hood! Because social distancing doesn’t allow her to do that right now, we’re hoping that this Town Guide offers everyone a glimpse of what Westport has to offer! 

** Of course, we’re not claiming to list ALL of Westport’s Gems (Come on, that would be impossible)! Below is a list of some of our favorites. If we’re missing something that you think should be on the list, we would LOVE to know in the comments. We will be adding and changing our Town Guides as we go to make sure that eventually, we get 'em all!  **IMAGES, unless otherwise noted are done by one of our fave local photographers, Julia D'ags!

        WESTPORT, CT -

        When it comes to picturesque New England towns-- Westport has it in the bag. Conveniently located in close proximity to NYC, Westport’s coastal community offers… just about everything. A bustling downtown with waterfront views, delectable restaurants, high-energy vibes, trendy shopping, charming architecture, pristine coast lines and some of the best public schools around.

        When it comes to entertainment, Westport has you covered! Offering up endless entertainment options, plenty of live music and activities... FOR DAY! There is so much that makes Westport a special place, and we hope this town guide gives you a small glimpse of what it has to offer!

        BEACH TIME 

        Westport Town beaches are open to residents in the summer months, but you can always purchase a day pass if you’re visiting from out of town. *Call Westport Parks & Rec for COVID restrictions & up-to-date day pass deets. 

        • Compo Beach: Compo Beach is, hands down, Westport’s most popular beach-- especially in the summer months! This 29 acre beach park is equipped with a boardwalk, pavilion, concession stand, two sand volleyball courts, large wooden playscape, bathroom facilities and lockers. 
        • Burring Hill: Understated and less busy than Compo, we love the vibes of this more low key beach. Bring a picnic for sunset and watch the fisherman off the Jetty! Pro Tip (park at GreensFarms Station and walk over if you don't have a sticker. shhh). 
        • Sherwood Island: Located in Westport, Sherwood Island is a State Park. This is a great option for out of towners looking to head to Westport to enjoy a beach day. We love Sherwood Island in the ‘off season’ because of the endless walking trails and bike paths!

        THE FOOD SCENE: 

        Westport food scene is a foodie's paradise. Weather you're looking for a girls night out, a bite with the kids, the perfect spot for a special date night or the perfect place for a BEC-- Westport has you covered. The options are endless, and we're only naming a FEW of our faves! 

        DATE NIGHT

        • Kawa Ni: Inventive Japanese & Pan-Asian plates to share and some of the most beautiful cocktails around. As explained by the legend’s themselves, Kawa Ni is “a type of Japanese drinking establishment which also serves food to accompany the drinks”. **May we suggest a Sake Bomb? Pro-Tip:  In the warmer months, don’t miss the roof top deck overlooking the river! 
        • Walrus Ally: This trendy, vibe-y pub style joint will give you all the feels. Walrus has the best live music in town during the warmer months and some of the best southern inspired eats around. 
        • Don Memo: Located in the original town hall in the heart of downtown Westport, Don Memo is a fun, creative take on Mexican fare.  Clean, vibrant food and drink that represent the true spirit of Mexico. Pro Tip- Make a reservation! 
        • Rive Bistro: Why is ‘water-view dining’ so rare in Westport?! Rive is a French Bistro featuring epic water views, patio dining and a  decedent menu that won’t disappoint. We love Rive for a special occasion. 
        • Parker Mansion: A classic go-to spot for us. Casual date night spot or the perfect place to meet a few friends. Parker has a fun ambience, friendly staff and a menu that will never disappoint. ** We love that they just opened a waterfront dining patio for the warmer months! 
        • Bar Lupa: Unbeatable Italian food with excellent service that will keep you coming back again and again! 
        • The Whelk: Located on the Saugatuck River, The Whelk offers a constantly changing menu featuring sustainable seafood and locally sourced produce. We love The Whelk’s communal tables, relaxed atmosphere and trendy vibes. (Pro tip- their oyster menu is shucking amazing)


        • Sherwood Diner: known by locals as “The Diner” (& let’s be honest, there really is no competition in this category) A long time, forever favorite of ours. May we suggest ordering: The Two Oh Three BEC (trust us on this one). 
        • The Granola Bar: A modern style ‘diner’ focused on healthy options for breakfast and lunch. Don’t miss their Turkish coffee! 
        • Sugar and Olives: More recently known as “Bad Ass Bagels”, Sugar & Olives has pivoted over the last few months and has quickly become Westport’s favorite bagel joint. Artisan bagels (and cream cheese) made with passion and love by a mother daughter team. Text your order to the bagel hotline— 203.816.0028

        LUNCH & CAFES 

        • Manna Toast:  Serving delicious, healthy & mindful eats that will blow your taste buds away! Manna Toast is a community driven cafe dedicated to serve locally sourced food in the heart of downtown Westport. We love their unique take on “toast” almost as much as we love the way it tastes! 
        • Terrain: Cafe, restaurant, and high end garden center. Terrain will give you all of the seasonal feels and leave you feeling inspired!  
        • Spotted Horse: A bustling atmosphere with a neighborhood vibe. This is one of our go-to local restaurants. An easy menu with options for everyone and a delicious take on your favorite comfort foods. We love their outdoor seating in the heart of downtown Westport.
        • Little Barn: Laid back casual pub with great food and fun vibes. This spot is one of our go-to spots for lunch or dinner and is perfect for families! (Pro tip: Check their live music schedule annnnd-- if you’re not with the kids, grab a high top table in the bar area). 
        • Sakura: We couldn’t write a town guide to Westport without an ode to one of our oldest favorites! Sakura has the best hibachi around and some of the best sushi in town. 


        • Gaetanos: If you’re looking for a classic New York style Italian deli (and let’s be honest, who isn’t) this place is the REAL DEAL. The energy is contagious from the moment you walk in the door and the food is almost too good to be true. Don’t be intimidated if there is a line out the door... it moves quickly & they pass out free samples! Don’t miss the buffalo chicken. 
        • Golds: Everyone loves a good old fashioned, authentic, Jewish Deli-- and Golds is a classic.
        • Fortunas's Deli: A long time staple in the Westport Deli scene. 


        • Stiles: This “hole in the wall” style market is locally loved by Westport-er’s, and for good reason. Stiles serves the freshest, locally sourced food and their quality is unmatched. (**Shockingly good sushi)
        • Fjord fishery: Premium, responsibly-sourced seafood market. 
        • Organic Market: The name says it all. Organic food, gourmet pre-made meals and specialty foods. 
        • Westport Farmers Market: One of the best Farmers markets around. Featuring a vast array of vendors, great vibes and an authentic community feel. Open Thursday’s from 10 to 2. A few of our fave vendors- Jane’s Pickles, Muddy Feet Flowers and Nit Noi Provisions. 

        LOCAL WATERING HOLES (Bars & Dive Bars) 

        • Black duck: Located on an old barge perched over the Saugatuck river, The Duck is a well worn and much loved icon. A Westport staple and a personal favorite. Sticky, grungy, and perfectly off centered. The eclectic decor, dim lighting, grumpy locals, heavy pours and juicy burgers will make your wildest dive-bar dreams come true. ** Pro Tip: get a seat on their new patio in the warmer months. Ohh, and the wings-- get ‘em extra crispy. 
        • Vivas: A locally loved Mexican joint with an awesome outdoor patio and lethal margs. *May we suggest the Cadillac Marg? 
        • Dunvilles: A Westport classic. This spot has some of the best burgers around. 


        • Grammie’s: Westport’s newest donut joint is an instant fan favorite. Serving up the yummiest donuts & biscuits made from the freshest ingredients.
        • Sunny Deas, Saugatuck Sweets: These are all great options for after dinner ice cream (or fro-yo) in with the kids! 

        TREAT YO' SELF

        Looking for something extra special? Mitchells Of Westport and Haus of Pretty are a few of Cindy's favorite local spots for luxury and pampering! For high end hair care and luxe shopping head to these spots... 


        • Haus Of Pretty: This high end salon just opened their new location in the heart of Saugatuck! Haus Of Pretty Specializes in the freehand hair painting technique known as balayage. If you’re looking for an extra special treat, this salon will not disappoint! At Haus of Pretty, they boast to be Westport’s Premiere Balayage Hair Salon (& we can't disagree). ** Haus of Pretty is also home to N. Lalor Photography's new photo studio! N. Lalor Photography creates beautifully clean images and specializes in portraits, professional head shots and branding images. 
        • Mitchells of Westport: Known for their exceptional customer service, exquisite designer clothing, jewelry and accessories, Mitchells is a long time staple in Westport. This high end designer retail store comes from humble beginnings and is known to be a family owned business with extraordinary service.


        • The Levitt pavilion: One of the largest and longest-running free outdoor festivals in the nation? SAYY WHAT! That’s right, free outdoor concerts, right in our backyard. This seasonal concert series right near downtown draws locals to set up yard chairs and picnics several times a week. 
        • Westport Playhouse: Broadway-quality theater, right here in Westport! This local play house is a locally loved haven for the arts, and certainly puts Westport on the Map!
        • MOCA: a visual and performing arts organization dedicated to creating arts experiences that enrich the lives of area residents and the entire community


        • Longshore: A unique and special crown jewel of Westport. Longshore offers golf, tennis, sailing and paddle boarding to town residents as well as day passes and parking passes for out of town residents. The property is equipped with an historic inn and delicious waterfront restaurant which is open to non-residents all year and is a popular spot for weddings and private events.
        • Wakeman Town Farm: This ‘Town Farm’ is open to the public and provides unique hands-on experiences and educational programs in agriculture and animal husbandry. Wakeman Town Farm strives to inspire the community and to promote a healthy environment and a more sustainable future. Special events, food and farm festivals, cooking classes and farm camps are just a few things that this special places offers 
        • The observatory: located at the highest elevation in town, the Westport Astronomical Society brings the wonders of the night sky to anyone who wants to experience it! This is a volunteer-run, non-profit organization that’s FREE and open to the public every Wednesday night from 8-10 pm (if the skies are clear). 
        • Earthplace: A 62-acre nature and wildlife sanctuary. Earth Place is great for families and offers an outdoor amphitheater, walking trails, picnic areas, and a 22,000 square foot learning center.

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