Why Essex, CT Was Just Voted the #1 Small Town in New England (And Why Moms Are Obsessed)

By Amy Ihrke, Grace & Haven · March 10, 2025 · 8 min read

When Yankee Magazine named Essex, CT the #1 small town in New England, we weren't surprised. We weren't even that excited — not because we weren't thrilled, but because if you've ever walked down Main Street on a warm Saturday morning with a scone in one hand and a coffee in the other, watching boats ease past on the Connecticut River, you already knew.

Essex doesn't need a magazine to tell it what it is. But we're glad the rest of the world is finally catching on.

As the owner of Grace & Haven, a women's and baby boutique right here on Main Street, I get to witness the moment people fall in love with this town every single week. The look on a mom's face when her kids squeal about the duck shop. The couple who came for a weekend and started Googling real estate by Sunday. The grandmother who cried a little at the Griswold Inn Hunt Brunch because it reminded her of another era entirely.

If you've been thinking about visiting Essex — or you live nearby and have been taking it for granted — consider this your invitation. Here is everything you need to know.

What Makes Essex, CT the #1 Small Town in New England?

Essex has been quietly doing everything right for a very long time. Founded in the 1600s and historically one of the most important shipbuilding ports on the Eastern Seaboard, it has never tried to be anything other than itself — and that authenticity is exactly why people keep coming back.

Here's what sets it apart:

• A walkable Main Street lined almost entirely with independent shops, restaurants, and galleries.
• The Connecticut River as its backyard, with marinas, boat parades, and some of the most stunning scenery in New England.
• A genuine, multigenerational community — the kind where the owners of the toy store have known your family for decades.
• History that you can actually touch: America's oldest continually operating inn, a steam train that's been running since 1871, and roads that remember the British.
• Events that feel like they were designed specifically for families and moms — because in many ways, they were.

The Yankee Magazine recognition is wonderful. But it just confirmed what those of us lucky enough to call Essex home have always felt.

The Top Things to Do in Essex, CT With Kids

If you're visiting with children — or planning a family day trip — Essex is genuinely one of the best options in the region. Here are the highlights:

The Essex Steam Train & Riverboat

This is the iconic Essex experience. The Essex Steam Train takes you along the Connecticut River through some of New England's most beautiful scenery — and then you transfer to a riverboat for the return trip. It sounds simple, but the magic of it gets kids every time. They also run special events throughout the year including Day Out with Thomas, a Murder Mystery Dinner Train, and the beloved North Pole Express at Christmas.

Sweet P's Ice Cream + The Ducks

Take your Sweet P's ice cream cone down to the town docks and feed the ducks — it's one of those small-town rituals that kids will ask to do again every single visit. Pro tip: get the SX Mud. Also: follow Sweet P's on Instagram, because they choose one name daily to win free ice cream.

Essex Duck

One of Main Street's most delightful surprises — Essex Duck is a rubber duck shop unlike anything you've seen. The selection is genuinely impressive, and kids go absolutely wild for it. Great for gifts, too.

Toys Ahoy

This is a Main Street institution. Dee and Alan have been running this toy shop for years, and the gift wrapping service alone is worth the trip. It's the kind of independently owned toy store that doesn't really exist anymore — which is exactly why you should support it.

The CT River Museum

The CT River Museum offers hands-on exhibits, river cruises, and a lecture series that's genuinely interesting for grown-ups. A great way to give the trip a little educational depth — and the views from the dock are spectacular.

Where to Eat in Essex, CT (A Mom's Guide)

This is where Essex really shines. Every single restaurant on this list is independently owned, chef-driven, and worth the trip on its own.

For Breakfast

For Brunch

For Dinner

The Best Places to Shop in Essex, CT

Main Street Essex is a genuinely independent shopping destination — every business is locally owned, thoughtfully curated, and worth your time.

For jewelry, don't miss Gillian Carson's Carson & Co pieces, available both online and in store. She's also written a wonderful local shopping guide if you want to go deep.

Where to Stay: The Riverbarn

If you're making a proper weekend of it — and you should — The Riverbarn is the answer. This converted barn on the Connecticut River is exactly the kind of place that feels like a warm hug from the moment you arrive. No detail has been overlooked. It books up, so plan ahead.

Favorite Essex Events (Don't Miss These)

Part of what makes Essex so special is its calendar — a full year of events that feel genuinely rooted in the community rather than manufactured for tourism.

• Daffodil Days — Spring arrives beautifully here. Main Street and the surrounding area burst into yellow, and the town comes out to celebrate.
• The Connecticut Spring Boat Show — The first in-water boat show of the season in New England.
• The Burning of the Ships Parade — A tongue-in-cheek annual celebration of the one battle Essex lost in the War of 1812. Only in Essex.
• Trees in the Rigging — Arguably the most magical Christmas event in Connecticut: an old-fashioned carol sing outside the Griswold Inn followed by a lighted boat parade where Santa arrives by water. Run by the CT River Museum and Essex Historical Society.
• FestiFall — Main Street in full fall glory, with activities for the whole family.

Grace & Haven: Your First Stop on Main Street

We opened Grace & Haven because we believed — and still believe — that shopping should feel thoughtful, calm, and meaningful. Our shop at 23 Main Street, Essex, CT carries women's clothing, baby and kids collections, and gifts for every person and occasion.

Whether you're visiting for the first time or you've been coming to Essex for years, we'd love to see you. Come in, take your time, and let us help you find something you'll love. And if you're shopping for someone else — our Gift Concierge is free, personal, and genuinely takes the stress out of gifting.

Can't make it in person? Shop our full collection online — every order is gift-wrapped, and shipping is always free.

Plan Your Essex Weekend

We could fill ten more pages with reasons to visit Essex — but honestly, the best thing we can say is simply: come. Walk Main Street on a Saturday morning. Let your kids feed the ducks. Have a scone at Savour and a cocktail at Noah's. Watch the boats move slowly down the river.

Yankee Magazine is right. But some things you just have to feel for yourself.