cigar factory outlet
 The Culture Carnivore's Guide To Norwalk, Connecticut
*This post originally appeared on Jessie on a Journey. A big thanks to Norwalk Now, who sponsored this Norwalk weekend!

As a New Yorker, I’m all about discovering local weekend getaways to escape the city. The thing is, my mind seems to automatically go to upstate New York, despite the fact that Connecticut is so close.

Actually, closer than my usual Catskills retreat, I learned, after taking the 40-minute train ride from Harlem-125th St Station in Manhattan to visit Norwalk.

If you’re wondering where to go in Connecticut, this hip city should definitely be on your radar. There is so much creativity to explore, whether through innovative cocktails, restaurant concepts, performance spaces and dishes (mac-and-cheese stuffed lobster, anyone?). They even have electric bike tours!

In all honesty, I was introduced to experiences I’ve never even had in NYC (because yes, I’m one of those New Yorkers who compares everything she does to life in the Empire State).

Want to have an awesome getaway in Connecticut? Swipe my active yet indulgent itinerary below, which explores the trendy South Norwalk (SoNo) and historic Wall Street neighborhoods.

Check out my 48-second trip video for a quick visual of the trip

Stay: EVEN Hotels Norwalk

While you certainly won’t find me dieting on the road, I am health conscious. I like to counter-balance my love of whiskey and bacon with being active, sleeping soundly and making sure I eat a proper diet (again, when the whiskey and bacon aren’t in front of me).

The wellness-focused EVEN Hotels Norwalk offered the perfect stay for this.

All rooms feature a workout area with resistance bands, yoga mats and yoga props that pair perfect with the free workout channels on the TV. For breakfast, flatbreads, smoothies and hot dishes laced with whole grains and quinoa offered a nutritious start to the day, while free bikes, ping pong and foosball kept being active playful.

Oh, and the bed; like sleeping on a cloud!

Price: When I visited in February 2018, weekend rates were about $99/night.

where to go in connecticut
Doing yoga in my room at EVEN Hotels Norwalk

SoNo Neighborhood

SoNo stands for South Norwalk. If you’re researching where to go in Connecticut with the goal of staying somewhere trendy, this is a great choice. Bonus: The South Norwalk Train Station — which connects with the Harlem 125th St and Grand Central Terminal stations in NYC — is walkable to these activities.

1. Get Active With An Electric Bike Tour

If you love exploring by bike, Pedego Electric Bikes SoNo puts a new spin on the old cycling adventure with electric bikes.

My first experience with an electric bike was while touring the hillside in the South of France, and I was psyched to see it’s becoming more popular in the USA. It’s incredible how easy these bikes make riding. In fact, they can assist you up to 20 mph. There’s also a throttle on the handlebar if you want to give your ride a little more oomph!

I did a short tour with the owner of the shop, who took me along the Norwalk River to a beautiful park called Oyster Shell Park, an ode to the city’s rich oyster heritage. The 25-acre greenspace is hugged by historic buildings, educational institutions and scenic walking trails. Nearby we also saw street art and a Second Empire-style mansion!

Rental prices start at $20/hour or $80/day.

Have you ever ridden an electric bike? In #Norwalk, this is a fun experience to try! Share on X
where to go in connecticut
How cool are these electric bikes?
where to go in connecticut
Cycling around Norwalk with Pedego
where to go in connecticut The Lockwood-Mathews Mansion Museum
The Lockwood-Mathews Mansion Museum

2. Elevate Your Boozy Brunch Experience

I did a lot of eating while in Norwalk, and Washington Prime offered a stellar brunch experience in a beautiful space. Chicken and waffles is my absolute favorite brunch dish (so good!), though their juicy thick-cut bacon may have stolen that title.

As they’re known for their steak, I also tried the carne rancheros featuring marinated hanger steak. The meat melted right in my mouth.

To pair, their beverage list goes beyond mimosas and Bloody Marys. While their “Manhattan Bar” options were tempting, when imbibing during the day I usually go for bubbly. My “Pearl Royale” — Prima Perla Prosecco and Creme Yvette Violette Liqueur with a twist — was light and refreshing.

Bonus: If you go during happy hour, they offer 50% off select appetizers, their raw bar and booze!

where to go in connecticut
Tasty dishes — and beautiful decor — at Washington Prime

3. Treat Yo’ Self Right

I’ll be honest; it’s rare that I get my hair properly done, as evidenced by my unbrushed look in Photo #1. Usually, I get a $25 cut-and-go at a simple salon near my apartment about four times per year.

So it was such a treat to have Thea Tsiranides — Master Colorist and the owner of Salon Être — work her magic on my limp locks. After getting a moisturizing mask and an incredible scalp massage, Thea gave me a blowout to give my hair some body.

I think the photos speak for themselves! This definitely added a confident pep in my step as I explored Norwalk.

where to go in connecticut
My Salon Être makeover

4. Learn The Art Of The Cigar Pairing

I’ve only tried smoking cigars a handful of times in my life, though never really knew what I was doing. And while I certainly still have a lot to learn, the family-owned Cigar Factory Outlet, established in 1932, put an educational twist on my visit.

Upon entering the shop — which is also a walk-in humidor — I was immediately greeted by Daniel, a cigar roller from the Dominican Republic who now rolls Nicaraguan tobacco in the shop. To the right is a lounge area with leather chairs and tables for hanging out with a cigar and a drink (yes, they have a liquor license!).

I had a small glass of cognac with a mild cigar, and smoked almost the entire thing while chatting with one of the owners, a legend in the cigar industry. Remember, no need to inhale; smoking a cigar is all about the flavors and aromas; plus, there’s much more nicotine than in a cigarette.

While you can get all kinds of different top tier cigars, they’re the largest retailer of Oliva Cigars in the world.

Note: To hang out in their lounge you’ll either need to be a club member and pay an annual fee, or spend $25+ in their retail shop.

where to go in connecticut
Watching Daniel hand-roll cigars at the Cigar Factory Outlet

5. Pair Bourbon & Beer With Burgers & Bacon

The “B” in the name Killer B SONO gives a nod to the restaurant’s focus on bourbon, beer, burgers and bacon — all of which they do extremely well.

Here, everything is a bit over-the-top (in a good way).

My first jaw-dropping moment came when my waitress brought over a smoked bourbon cocktail — literally smoked tableside in a glass box. When the box door opens, delicious smoke wafts out like a magic act.

Next up: a three-pound lobster stuffed with macaroni and cheese. Now, this isn’t just any lobster; but a “lazy man’s lobster,” so chunks of meat are removed and easy to grab.

Finally, a bacon flight featuring 10 pieces of uniquely spiced or glazed bacon. The pieces dangle from a wire, while the waitress torches each individually for extra crispness.

During happy hour, every patron gets a free piece of bacon with their drink order. Yum!

where to go in connecticut
A decadent meal at Killer B’s

6. Hit The Beach, Japanese Style

For an elevated nautical experience, The Beach House offers a tasty and modern trip to play in the sand. And when I say play in the sand, I really mean drinking the most delicious coconut mojito you’ve ever tasted (seriously, it tasted like a coconut creamsicle).

The space is really modern, with lots of wood furnishings and exposed dangling bulbs intertwined with boat line. Nautical elements like ocean blue hues and open treasure chests remind you where you are, as does the tasty seafood.

What’s really unique is the food has a Japanese twist, thanks to owner Kane Xu, who shared stories about each dish as I ate. While Xu travels to NYC’s Chinatown to get the wonton skins for the goat cheese wontons served with pepper jelly, the New York Strip Steak features a gorgonzola crust and Japanese “seven spice” (shichimi togarashi).

I absolutely loved the Oysters Rockefeller, made with fresh blue point oysters and swapping in bacon fennel cream for crust (so you can actually taste the shellfish!).

Love #brunch? Norwalk offers a weekend escape from #NYC full of hip, boozy options! Share on X
where to go in connecticut
A tasty and boozy lunch at The Beach House

7. Savor A Delicious Spread & DIY Bloodies

If you’re the type who likes to dine family-style and try a variety of dishes, The Spread is a great choice with a hip atmosphere. I was fortunate enough to visit during brunch, where the drink options included everything from a DIY Bloody Mary bar (oh, the bacon!) to creative cocktails like the “Bonfire” featuring gin, mezcal, fresh lemon, egg white, simple syrup and bitters (pictured below!).

The energy is lively as groups pass plates like Nutella-laced crepes featuring fresh fruit and creamy grits topped with egg and tender braised brisket. Dishes feature local ingredients from purveyors like Olivette Olive Oil, Harbor Harvest and Copps Island Oyster.

Bonus: Thursday, Friday and Saturday the restaurant clears away the tables and turns their space into a fun dance party!

where to go in connecticut
Tasty brunch dishes at The Spread

8. Shop Local On Washington Street

This is the main thoroughfare of SoNo, where you’ll find tons of independently owned restaurants, bars, galleries and shops.

One shop I spent time in was Simple SONO, a high-end boutique focused on really soft, durable fabrics and hand-made garments from Europe and the USA. It’s the type of place where you buy a sweater that lasts 15+ years, or Egyptian cotton bed linens that make you feel like you’re literally sleeping in heaven.

Their staff is also super helpful if you’re in need of some style advice.

Just note: with high quality comes a high price tag, so make sure to bring your credit card. They did have a quite a few items of sale, too, which made it much more affordable.

where to go in connecticut
Trying on new clothes at Simple SONO

9. Transport Yourself To Ireland

After a weekend of exploring Connecticut’s hippest spots, our final beer was sipped in a classic Irish pub.

Called O’Neill’s Pub & Restaurant, brothers Ollie and Michael O’Neill opened the establishment on St. Patrick’s Day of 1999. Both inside and out, the building has an Irish feel, from the brick façade with arched doorways and windows to the art showcasing Irish countryside to the celtic knots woven into the interior design.

And of course, the menu. Sure, you can watch the game while filling up on nachos and chicken tenders; but you’ll also find “O’Neill’s Specialties” paying homage to the O’Neill’s hometown of Tipperary.

Try the Old World Beef Stew featuring tender morsels of beef served in a thick gravy with carrots, celery and onions. Another recommendation: the Mild Irish-Style Chicken Curry on saffron rice.

Who knew you could find a slice of Ireland in Connecticut? Yum! #NorwalkNow Share on X
where to go in connecticut
Kickin’ back at O’Neill’s Pub & Restaurant

Wall Street Neighborhood

10. Mix Juke Joints & Rooftops

All under the same roof, actually. At Peaches Southern Pub & Juke Joint you’ll get an amazing mix of live music, southern fare, craft cocktails and rooftop views.

Oh, and did I mention a happy hour with $4 beers, $5 wines and $6 cocktails? And they’re cocktails are really, really good!

On the first floor you’ll savor dishes like “Dark and Stormy Ribs” done in a ginger-rum glaze, a house-burger laced with fried green tomatoes and pimento cheese, and “Panhandle Shrimp & Grits” in a savory shrimp gravy.

After dinner, head upstairs to enjoy the patio or hit the dance floor to shake off those calories to a live band.

where to go in connecticut
Dark & Stormy Ribs. Yum! Photo via Peach’s Southern Pub & Juke Joint.

11. See A Show At A World-Class Theater

Originally opened in 1915 as The Regent, the Wall Street Theater just re-opened in May 2017 after a $10 million revamp.

While over the years the theater has changed names and purposes — with past acts ranging from Wu-Tang Clan to Living Colour and beyond — today this nonprofit National Register of Historic Places theater hosts live acts in a gorgeous space featuring multi-level seating for about 1700 (including standing room), a restored stage and live streaming capabilities.

During my stay, I saw an incredible show featuring Allman Brother Johnny Neel performing with the Screamin Eagle Band. Neel is blind, but that doesn’t seem to affect his extraordinary keyboard playing. A local band of young men played as their opening act, and Neel asked their lead singer to come out on stage and play harmonica with him and his act. It was a wildly touching moment (I may have teared up cried).

The Wall Street Theater is more than just concerts, though. Also expect comedy shows, live improv, fitness events, talent competitions and more.

where to go in connecticut
Seeing Allman Brother Johnny Neel play with Screamin Eagle Band

12. Experience Norwalk’s Funkiest Underground Space

For a grittier performance experience, head to Factory Underground Studio.

While I didn’t get to see a show there myself, I did get a tour of the funky space. The large entrance room features quirky art — I loved the rusted doors hanging like paintings from the walls — and they sometimes do gallery shows.

Wandering the rest of the space, there are many recording rooms in various sizes, and even a large room for recording music videos and where concerts are held (pictured below).

If you want to hear good music in a chill spot, definitely check out their events calendar.

where to go in connecticut factory underground
Photo via Norwalk’s Factory Underground

What are your favorite Norwalk experiences? Please share in the comments below! 

Liked this post? Pin it for later!

The Culture Carnivore's Guide To Norwalk, Connecticut


Getting There: You can take Metro North from either Grand Central Terminal or Harlem-125th to the South Norwalk Station. Off Peak tickets are $6.25 one way and Peak tickets are $8.25 one way.

Getting Around: The EVEN Hotels Norwalk was about a 10-minute Uber ride from SoNo, so it was affordable to get around this way. Most of the rides were about $10-$12 one way. Once you’re in SoNo, it’s easy to walk around. Even walking to the Wall Street neighborhood only takes about 30 minutes on foot, depending where you are.

Note: You can also get around by bike. EVEN Hotels Norwalk offers free bike rentals, and Pedego offers daily and multi-day electric bike rentals starting at $80/day.

Packing Essentials: Norwalk is a safe city, though no matter where I go I always pack a few safety essentials, including:

Check out my 48-second trip video for a quick visual of the trip

Jessica Festa

Jessica Festa is the editor of Epicure & Culture as well as Jessie on a Journey. She enjoys getting lost in new cities and having experiences you don’t read about in guidebooks. Some of her favorite travel experiences have been teaching English in Thailand, trekking her way through South America, backpacking Europe solo, road tripping through Australia, agritouring through Tuscany, and volunteering in Ghana.

You may also like...

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.