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Nothing goes hand in hand quite like summertime in New England and going boating. Whether it’s taking a sailboat out on sunset, a daytime cruise on a Chris Craft or getting from point A to point B by ferry – which is a classic New England form of summertime transportation, as you can read about in our summer spots worth a ferry ride to post, boating is apart of a New England lifestyle whether you own one or not. Since this year a lot of time will be spent doing social distance activities like boating locally – I wanted to put together a few guides focused on towns you can explore via boat. Today we’re going to kick off this series of posts with five towns to dock at & explore along the Connecticut River.

Essex, Connecticut

Essex is by far one of my favorite places to explore along the Connecticut River. With gorgeous historical homes to admire, a variety of restaurants from seafood to sandwich shops to choose from, and a coffee shop to top it all off – Essex Connecticut has it all and then some. Due to the fact that the current can be strong in this area, we typically pay for hourly docking at Brewer Essex Island Marina. This marina is actually on its own island equipped with a ferry to passenger visitors over to downtown Essex in a matter of just minutes. Now if paying for docking isn’t in your budget you can always take your chance on the town dock at the base of Main Street which I believe offers free docking, up to two hours – but don’t quote me on that!

If Essex seems interesting to you here’s a few places to check out while you dock:

SHOPPING: Click Here for a list of my favorite Antique Shops in Essex like  Weltner’s Antiques & Art.

FOOD: A few of my favorites are The Black Seal for seafood, Olive Oyl’s for sandwiches, and The Griswold Inn for anything else!

COFFEE: Make sure to check out one of my favorite coffee shops in Connecticut, Essex Coffee & Tea which I often feature on my Instagram as seen here.

MUSEUM: Connecticut River Museum preserves the history of The Connecticut River and the towns alongside it.

Old Saybrook, Connecticut

Old Saybrook is typically where we dock and gas up before crossing The Long Island Sound to Montauk or The Hamptons. While it’s a great place to break up the trip for anyone heading downriver, it’s also a great place to explore along the Connecticut River and enjoy a mini-staycation. A few times we’ve gone downriver and docked for an overnight stay at the gorgeous Saybrook Point Inn which includes a shuttle service to the historic main street, Old Saybrook closer proximity to Foxwoods and a mini-golf course just walking distance next-door! Not to mention the Saybrook Point Inn has a spa worth the trip up & down the river.

If Old Saybrook seems interesting to you here’s a few places to check out while you dock:

SHOPPING: Click Here for a list of my favorite Antique Shops on the Eastern Connecticut shoreline, like Antique Depot & more!

FOOD: A few of my favorites are Penny Lane Pub for a burger or Johnny Ad’s for fried clams and lobster.

COFFEE: Ashlawn Farm Coffee is a great local coffee shop to start your day off with a visit when in Old Saybrook. While The James Pharmacy B&B is a great place to end the afternoon with gelato and a foamy cappuccino, they have the most stunning espresso machine!

HISTORIC HOMES: Take in the view of what used to be Katherine Hepburn’s cedar-shingled home along with many other New England beachside manors over on Fenwick, just walking distance from Old Saybrook Point Inn.

East Haddam, Connecticut

Further up the river from Essex & Old Saybrook is East Haddam Connecticut. This town is a quaint New England town with charm comparable to being in a Gilmore Girls episode. When visiting East Haddam we usually dock right up to the Goodspeed Opera House’s private dock on the Connecticut River, just steps away from the theatre. Make sure to call 860.873.8664, ext. 333 for information and docking reservations especially if you have plans to visit the Goodspeed Opera House for an event!

If East Haddam seems interesting to you here’s a few places to check out while you dock:

SHOPPING: Goodspeed’s Station Country Store is the perfect place to experience a good old fashioned New England country store. From a retro candy bar to puzzles galore – this place is ideal for gift giving if you ask me.

FOOD: For romantic patio dining with a view of the river I highly recommend The Gelston House and if you’re really hungry you have to visit La Vita for Italian food and patio dining.

BREAKFAST & COFFEE: We definitely recommend a visit to Higher Grounds at 32 Main, whether your visiting for just a cup of coffee or a breakfast burrito – this place is good.

HISTORIC LANDMARKS: If you visit East Haddam you have to take in the view of the Goodspeed Opera House adjacent to the East Haddam historic drawbridge first opened in 1913!

I hope this post inspired you to pull up anchor and explore along the Connecticut River this summer. As for the perfect boating attire for the Connecticut River – I recommend pants and a short sleeve sweater or blouse. Truthfully we’ve had a cooler summer so when the wind picks up it can be quite cold on the river. On this specific day, I was wearing head to toe Red Fleece, which is a brand you all know I adore. I recently had received this navy puff-sleeve sweater that fits true to size, in the mail, and within a week of owning it – I went out and purchased one more. I love how comfortable and effortless they are, as the puffed sleeve effect makes it a versatile item worthy of work or an evening out on the water. On this trip, I paired the sweater with a pair of white wide-legged cotton pants and a nautical wide woven belt to complete this nautical navy and white attire. Overall, I hope you found this post insightful and don’t hesitate to leave a comment down below of any other New England dockable spots you’d like me to showcase here next.

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