On the evening of Friday, December 4, a DJ will be set up at Town Hall. Victorian carolers will work Main Street, toy soldiers will be posted along the sidewalks and horse-drawn carriages will give rides, all free, from 6 to 9 p.m. Most people know the Ridgefield Chamber of Commerce's Holiday Stroll as the start of the season, with its December 4–5 dates.
This year the calendar shows the Stroll near the end of the season. Three organizations open their own holiday markets in November, a week or so apart. The Chamber goes first, then the Ridgefield Guild of Artists, then Keeler Tavern Museum. By December 4, the Guild's sale has been open for three weeks and Keeler's for two, and both keep going after the carolers have left.
November 5: the Chamber puts eighteen storefronts on one list
The first of the three is Sip & Shop, on Thursday, November 5, from 5 to 8 p.m. The Ridgefield Chamber of Commerce organizes it. The Chamber's listing says the evening is for getting a head start on holiday shopping.
The participant list includes more than gift shops:
- Gifts, jewelry and design: Addessi Jewelers, Desires by Mikolay, Jill Rae Designs, Rachel Gedymin Design LLC, Make-Modern, Flipping Creative
- Home and antiques: Lilia Antiques & Interiors, Olley Court, Plank Ridgefield, reFabjack
- Apparel and active: BrandNu Apparel, CT Run Co
- Wellness and beauty: Susi Laura Massage, The Gift MedSpa, ReviveX, PELO by EDGARDO
- Wine and art: Sommlike, The Aldrich Contemporary Art Museum
The Aldrich's place on that list sets up the rest of the month. A contemporary art museum is taking part in a retail night, and the next two openings are also run by cultural nonprofits rather than shopkeepers.
For a sit-down stop, the Chamber points shoppers to Terrasole, which is running an extended happy hour all night. The Chamber says more details, including any route map, are still to come, so check its page before you head out.
November 13: the Guild's seventeenth Festive Home
Eight days later, the Ridgefield Guild of Artists opens Festive Home 2026, its 17th annual holiday marketplace. It carries handmade work from more than 50 artisans: ornaments, cards, knitwear, candles, pottery, holiday décor and member art.
The timing works in two steps:
- Friday, November 13, 5 to 7 p.m.: a preview fundraiser, which gets you in before the public opening.
- Saturday, November 14, through Sunday, December 13: open shopping, Tuesday through Friday from noon to 5 p.m. and weekends from 11 a.m. to 5 p.m.
The Guild closes Monday through Thursday, November 23–26, for Thanksgiving and reopens Friday, November 27. That makes the Friday after Thanksgiving a reopening day at the Guild. Its building is at the end of Halpin Lane.
November 19: Keeler Tavern's Carriage Barn becomes a shop
The third opening is on Main Street. Keeler Tavern Museum's Holiday Boutique opens in the Carriage Barn on Thursday, November 19, and runs through Sunday, December 20. Hours are Thursday through Sunday, 11 a.m. to 4 p.m., and admission is free. The museum describes the stock as curated gifts, décor and one-of-a-kind goods from local artisans, including items made and sourced locally. The Carriage Barn is part of the Keeler Tavern Museum & History Center at 152 Main Street.
Earlier in the month, the same campus hosts lectures in the Garden House. The Tavern Culture Series talk "Western Expansion in the Early Republic" is Sunday, November 8, at 2 p.m. On Thursday, November 12, at 7 p.m., Nina Sankovitch speaks on "Universal Friend: Forgotten Hero of the American Revolution." Both require registration. If you've come to know the property through its fall lectures, the November 19 opening is when it starts selling holiday gifts.
The weeks when everything is open at once
The three openings overlap with the regular cultural calendar. The table runs from Sip & Shop to the Stroll and pulls from the Ridgefield Playhouse, The Aldrich and The Prospector along with the three markets.
| Date | What's on |
|---|---|
| Thu, Nov 5 | Sip & Shop, 5–8 p.m.; Michelle Wolf at the Playhouse, 8 p.m.; The Cat in the Hat and Wild Horse Nine open at The Prospector |
| Sat, Nov 7 | Co-Create, A Family Art Adventure at The Aldrich, 10:30 a.m. |
| Sun, Nov 8 | Tavern Culture Series at Keeler, 2 p.m. |
| Thu, Nov 12 | Nina Sankovitch at Keeler, 7 p.m. |
| Fri, Nov 13 | Festive Home preview fundraiser, 5–7 p.m. |
| Sat, Nov 14 | Festive Home opens; Playhouse Fall Gala with John Legend, 8 p.m. |
| Thu, Nov 19 | Keeler Holiday Boutique opens; Being Heumann at The Prospector, 7 p.m. |
| Sat, Nov 21 | Free admission at The Aldrich for Third Saturdays, from 10 a.m.; Lou Gramm at the Playhouse, 8 p.m. |
| Tue, Nov 24 | Hexed opens at The Prospector |
| Fri, Nov 27 | Festive Home reopens after Thanksgiving |
| Sat, Nov 28 | The Irish Tenors with the Ridgefield Symphony Orchestra at the Playhouse, 8 p.m. |
| Sun, Nov 29 | Sunday Afternoon Tour at The Aldrich, 2 p.m.; Judy Collins at the Playhouse, 7:30 p.m. |
| Mon, Nov 30 | Judy Collins at the Playhouse, 7:30 p.m. |
| Fri, Dec 4 | Keeler Holiday Stroll Open House, 5–7 p.m.; Holiday Stroll, 6–9 p.m. |
From November 19 on, the Guild and Keeler are both open Thursday through Sunday, apart from Thanksgiving week, when the Guild is closed through Thursday. That gives you two places to shop for handmade gifts, both run by nonprofits, within a short drive of each other on any of those weekends.
Saturday, November 21, is the easiest day to fit everything in. The Aldrich has free admission from 10 a.m. for Third Saturdays, Keeler's boutique opens at 11, the Guild opens at 11 for its weekend hours, and Lou Gramm plays the Playhouse that night.
On November 14, the Guild's first public day is also the night of the Playhouse gala with John Legend. The Playhouse listing showed the gala as sold out, so check availability before planning around it.
Dinner between stops: The Mariner Tavern is back
One familiar Main Street dining room is back after spending most of this year closed. The Mariner Tavern at 451 Main St. opened on September 9 after an eight-month renovation, the Ridgefield Herald reported.
The address has a long history in Ridgefield. Tom Quinn founded The Ancient Mariner there in 1974. Jessica Wilmot started as a waitress in 1978 and later bought the business, then ran it for three decades before selling it to chef Shannon Sturz in the spring of 2025. Sturz opened in May 2025 and closed that January to rework the space for functionality. He brought in designer Christian Arkay-Leliever to refresh the bar, dining room and bathroom.
Regulars will still find the ship's wheel, the wooden barrels at the host stand and bar, and the front door with the peephole. The bar now has light wood paneling and a copper ceiling, and a plaid booth wraps around to a new kitchen window. The menu keeps its seafood and old favorites like wings and fish and chips. It adds a meat program with prime cuts, duck and chicken, and pasta that can be made gluten-free.
Sturz told the Ridgefield Herald what he wants the restaurant to be:
"I want this to be an extension of your home."
Plan around its hours. The Mariner Tavern serves lunch and dinner Wednesday through Friday and brunch and dinner on weekends, and it is closed Monday and Tuesday. It's open for dinner on Sip & Shop night, a Thursday, and for weekend brunch before a Saturday at Keeler and the Guild. It won't work for the Monday, November 30, Judy Collins show, and you can check hours and menus at themarinerct.com.
December 4: the Stroll is the finale
By the night of the Holiday Stroll, Festive Home has been open since November 14 and Keeler's boutique since November 19. Keeler opens the museum that evening for its Holiday Stroll Open House, 5 to 7 p.m., an hour before the free downtown program starts at 6. The Chamber's page still lists December 4–5 with programming details to come.
Neither market closes with the Stroll. The Guild's sale runs through Sunday, December 13, and Keeler's Carriage Barn stays open through Sunday, December 20. If you miss the November openings, the Guild is open for nine more days after the carriage rides, and Keeler for sixteen.
If you'd like to talk about how local seasons like this one fit into your plans for home, Heather Lindgren would love to hear from you. Contact Heather to discuss your next move.
