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| Is it humiliating for a turkey to be Easter egg colored prior to Thanksgiving? Perhaps. But these are the birds at Gozzi's Turkey Farm in Guilford that get to live! |
A Fun, Festive Connecticut Weekend After Thanksgiving
Much of this itinerary—custom-curated by your truly—works beautifully throughout December and into the new year. See the footnote at the end of this post for details.
Do you have family and friends joining you in Connecticut
for Thanksgiving—and maybe sticking around through the weekend? Once the feast
is behind you and the Macy’s Parade and Westminster Dog Show fade into happy
memories, you’ll find no shortage of things to do.
Here’s a relaxed, fun, very-Connecticut Friday and Saturday
itinerary to enjoy once everyone has slept off the turkey tryptophan.
Friday, November 28
Ease Into the Day (Breakfast = Leftovers, Obviously)
Take your time getting up. You’ve earned it. And let’s be
honest—you already know what breakfast is: eggs, fruit, and a
turkey-and-cranberry-sauce sandwich. It’s practically a rule the day after
Thanksgiving.
Midday Shopping Along the Connecticut River
Once you’re vertical, head toward the oh-so-charming
villages along the Connecticut River to kick off (or continue) your holiday
shopping.
Essex and Chester are classic small-town New
England—artsy, quaint, quietly festive. No inflatable snow globes here. These
are real-deal holiday villages with personality.
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| Main Street Essex |
First Stop: Essex
Lunch: Grab a bite at Black Seal Seafood Grill
on Main Street. Cozy, unfussy, perfect. (https://theblackseal.net/)
After lunch, take your time strolling through Essex Village.
Main Street is lined with unique shops ideal for one-of-a-kind gifts—the kind
your friends will say, “Where did you find this?”
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| Annual Holiday Train Show at the Connecticut River Museum |
Pop into the Connecticut River Museum for sweeping river views and the annual Holiday Train Show. The layout changes every year, and every year it becomes its own little world. Magical. (https://ctrivermuseum.org/)
Cocktail Hour at The Griswold Inn
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| "The Gris" |
It's Five O'Clock somewhere! Duck into the Tap Room at the Griswold Inn (“The Gris”), one of the oldest continuously operating inns in the U.S., running since—wait for it—1776. (https://griswoldinn.com/)
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| "Griswold House" by Neil MacEachern |
Personal Note: See the painting of the inn hanging above the fireplace in the reception area? My uncle, Neil MacEachern, painted it. I admired it for years before realizing it was his—he spent the summer of 1930 painting scenes up and down the River. Small world, right?
Dusk in Chester: A Holiday Warm Glow
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| Starry Night in Chester |
Chester’s Main Street curves gently through the village and feels like walking through a handmade holiday card—especially at dusk.
Dozens of lighted stars hang from rooftops, cluster around
shop windows, and shimmer from wires above the street. It’s subtle, warm,
nostalgic… absolutely charming.
Dinner Options
- River
Tavern — Fantastic but small, so reservations can be tricky this time
of year. (https://www.rivertavernrestaurant.com/)
- Marker
37 — A wonderful riverfront spot with great food. Make a mental note
to return for al fresco dining in summer. (https://www.markerthirtyseven.com/)
Saturday, November 29
Morning at the Florence Griswold Museum (Old Lyme)
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| "Painted Palettes" (top) and Miss Florence's Dining Room |
Begin the day at the Florence Griswold Museum, the home base of American Impressionism. Explore Miss Florence’s historic boardinghouse, where artists like Childe Hassam and Willard Metcalf once painted murals directly on the doors (legend has it the dining room murals were done during a particularly boisterous weekend while Miss Florence was away).
In December, the house is transformed for a 1910-style
holiday celebration—period décor, festive table settings, and beautifully
curated displays.
Don’t miss the Krieble Gallery, where today's artists
decorate the holiday trees as part of the museum’s “Painted Palettes”
tradition. It’s clever, colorful, and always a delight.
(https://florencegriswoldmuseum.org/)
Lunch Stop: Hadlyme Country Market
Grab sandwiches, wraps, or a personal pizza—simple and satisfying—the market has been serving wayfarers for 120 years. (https://www.hadlymecountrymarket.com/)
Afternoon Adventure: Gillette Castle State Park
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| Gillette Castle |
Next, head up to Gillette Castle in East Haddam, perched high above the river. Built by actor William Gillette, who toured North America and England for more than three decades in his own version of Sherlock Holmes, the castle is quirky, medieval-ish, and full of hidden surprises. (https://ctparks.com/parks/gillette-castle-state-park)
 |
| William Gillette as "Sherlock Holmes" |
Take in the crisp air on the surrounding trails, then step inside to see the castle decked out for the holidays. Secret doors + festive décor = a holiday outing no one forgets.
Evening Finale: Mystic Lighted Boat Parade
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| Mystic Lighted Boat Parade |
Cap off the day in Mystic for the beloved Lighted Boat Parade. Boats big and small drift along the river covered in lights, holiday scenes, and creative displays. It’s festive, cheerful, and very Mystic.
Best Viewing Tip: The riverbank at the Mystic
Seaport Museum is ideal, and admission after 5:00 PM that night is just
$10/person.
The parade takes place at 6:15pm so there's plenty of time for dinner. My pick would be The Shipwright's Daughter (https://www.shipwrightsdaughter.com/) but good luck getting a reservation that night, so save it for another special occasion. How about driving up to East Haddam for dinner at The Gelston House next to Goodspeed Opera House. A post-8:00pm reservation (after the curtain has gone up on Goodspeed's production of White Christmas) may be possible. (https://www.gelstonhouse.com/)
Footnote: Enjoy These Gems All December Long (and
Beyond!)
With the exception of the Lighted Boat Parade, nearly
everything on this itinerary is just as wonderful throughout December—and many
experiences extend well into the rest of the year:
- Essex
and Chester are pure holiday magic in December, but their boutiques,
galleries, and cafés make them fantastic year-round destinations for
one-of-a-kind shopping and leisurely wandering.
- Local
restaurants shift with the seasons—cozy in winter, lively in spring,
breezy in summer, and glowing in autumn. No two visits feel quite the
same.
- Miss
Florence’s boardinghouse is open year-round, and the lovingly restored
1910-era gardens are a treat in warm weather. If you look closely at some
of the paintings created by the museum’s artist boarders, you can spot
those very flowers immortalized on canvas.
- Gillette
Castle closes for the season on December 21 and reopens in spring, but
the surrounding state park stays open all year. The trails and sweeping
Connecticut River views are spectacular in any season—frosty mornings
included.
Thinking about a move to Connecticut? Or maybe you're already here and ready to upsize, downsize, resize—or rightsize. Wherever you're headed, I'm here to help. The search for a home is more than a transaction—it’s a journey, and I’d be honored to take it with you.
Let’s talk.
