Here’s our relatively exhaustive list of pop-up boutiques, holiday events, concerts, tree-lightings, strolls, and shops that do it up for the season.

Pop-Up Holiday Shops:

Artistry at the Guilford Art Center – Over 300 fine American crafters, artisans and jewelers are featured at this celebrated annual sale, open thru 1/8/23. Hours: Monday through Saturday, 10am-5:30pm and Sunday 12-5pm. Details.

Florence Griswold Museum Shop is all stocked up with ornaments, children’s toys, books, jewelry and gifts for the holidays — complimentary gift-wrapping included. Online shopping, too! Visit Flo Gris.

Stone Acres Farm Holiday Markets, 11/19 – 12/30, 10am – 6pm: The farm-stand will offer perfect holiday gifts crafted by local artisans, local xmas trees and farm-raised holiday turkeys! Updates coming soon.

Wesleyan Potters Annual Exhibit and Sale: 11/25 – 12/24, 10 – 6pm, Wed, Thurs, Sat, Sun and 10 – 8pm Fridays: Discover a vast selection of original, handcrafted pieces: sparkling jewelry, fun and functional pottery, statement sculptures, elegant hand woven apparel, original woodwork and more. Find out more.

Hill-Stead for the Holidays, Hill-Stead Museum, 11/26 – 1/5: Beginning the day after Thanksgiving and continuing through early January, the former Pope family mansion is decorated for the holidays. The Annual Holiday Boutique features 25 artists and crafters who bring their best to this two-day sale, 12/3 & 12/4. Preregistration required for boutique. Visit Hill-Stead.

East Haddam Holiday Market, 11/26 from 11 – 3pm: A collection of artists, specialty artisan products, holiday-inspired vendors, prepared foods, and talented local musicians. Get the details.

Holiday Market at the Westbrook Outlets, 11/26, 10 – 4pm: Find a great selection of local artisans featuring unique offerings like accessories, apparel, baked goods, candles, jewelry, soaps, woodworking, and much more! Details.

Chester Holiday Market: 11/27, 12/4, 12/11, 12/18: Every Sunday between Thanksgiving and Christmas, enjoy farmers, special events, openings and more in the shops and restaurants of Chester from 10am – 1pm. Learn more.

Holiday Shopping Extravaganza at Chester Meeting House, 12/2, 5 – 8pm: Held at the Historic Chester Town Meeting House, HSE is always a friendly, festive event full of amazing local vendors, gorgeous gifts, handmade goods, and plenty of Holiday Cheer! Find out more.

Dudley Farm Museum Open House and Holiday Market, 12/3, 12/10, 12/17: Specialty items from vendors will be sold in and around the Munger Barn. On 12/3 the Farmhouse will be decorated for the season and refreshments served. Visit their website for current info. 

Wadsworth Mansion Holiday Bazaar, Middletown: Sunday, 12/4, 10 – 3pm:  Featured vendors from the Open Air Market will be selling handmade products and unique holiday gifts for your family and friends. Visit Wadsworth Mansion.

Secret Seller Holiday Market, 12/10: Local arts, crafts & food from 10 – 4pm (this is a good one!) at Deep River Historical Society. Read more.

Higganum Holiday Pop-Up Market, now thru 12/15: Locally handcrafted products, made with love at 3 Candlewood Hill Road, Higganum. Read more.

Historical Society Christmas Fair at Parmelee Farm, Killingworth  12/3, 8:30 – 3pm: Parmelee Farmhouse will be transformed into a holiday boutique with lots of handmade items crafted by members, including live arrangements, baked goods, holiday decor, gift items, knitted accessories. Parmelee Farm, 465 Route 81, Killingworth. Check soon for updates.

Mood Music:

There’s no better way to celebrate the season than a holiday chorale or concert.   

Winter Wonderettes at Ivoryton Playhouse, 11/17 – 12/18: This seasonal celebration finds the girls entertaining at the annual Essex Hardware Holiday Party. When Santa turns up missing, the girls use their talent and creative ingenuity to save the holiday party! Featuring great ’60s versions of holiday classics such as “Santa Claus Is Comin’ to Town,” “Jingle Bell Rock,” “Run, Rudolph, Run,” and “Winter Wonderland,” the result is, of course, marvelous! This energetic and glittering holiday production is guaranteed to delight audiences of all ages. Get tickets.

Musical Masterworks, Old Lyme Congregational Church, 12/3 at 5pm & 12/4 at 3pm: Immerse yourself in MM’s performance in the accoustically spectacular church: J.S. Bach, Gamba Sonata in G Major, BWV 1027 (arr. for violin, cello and bass), Edgar Meyer, Trio 1, Rossini, Duet for Cello and Bass in D Major, Edgar Meyer, Trio 3. Get tickets here. 

Cappella Cantorum Hallelujah!,12/4: The Cappella Cantorum Masterworks Chorus will perform musical selections including:Gloria (Antonio Vivaldi), O Magnum Mysterium (Morten Lauridsen) and more at John Winthrop Middle School Auditorium in Deep River. Find out more.

Con Brio Christmas Concerts at Christ The King Church, Old Lyme on 12/9 at 7pm and 12/11 at 3pm: Forrest Jubilate Deo (2016), for soloists, chorus and orchestra, conducted by Dr. Stephen Bruce. Con Brio welcomes Carley DeFranco, soprano, and welcomes back Allison Messier, mezzo-soprano. Purchase tickets.

Essex Winter Series, 12/18: Brentano String Quartet with Mihae Lee. Get tickets.

Messiah Sing Along at The Kate,12/18, 2pm: Participate in the sounds of the season with a Kate holiday tradition. Open to all who want to sing-along, the Messiah Sing combines Cappella Cantorum’s professional soloists with a chorus of talented volunteers. Sit in the back and listen or sit down front and participate. Singers should arrive at 1:30 for section seating and rehearsal. Purchase tickets here.

Connecticut Early Music Society Presents Handel’s Messiah, 12/20 7pm: Ian Watson, Artistic Director for Connecticut Early Music Society conducts a performance of Handel’s popular choral work, Messiah, on Tuesday, 12/20 at 7:00 P.M. in Harkness Chapel on the Connecticut College campus. Get tickets here.

Get in the holiday mood with these upcoming events:

The E List Girls’ Nights Out: Drinks, Discounts, and Dinner! Guilford on 12/8. Details here. 

Christmas in Connecticut at The Goodspeed, 11/18 – 12/30: Based on the classic 1945 Warner Bros. film, this World Premiere musical comedy is a delightfully cheerful way to celebrate the holiday season! Get tickets here.

Deck the Walls at Lyme Art Association, 11/19 – 1/2: Juried exhibit of Lyme Art Association members. This exhibit of well-priced artworks is perfect for gifting! Find out more.

The Nutcracker, Short & Suite at Wadsworth Mansion, Middletown, 11/20, 3 performances: The Mansion welcomes Ballet Hartford for an intimate performance of a classic holiday favorite. This is a condensed version that features a combination of dance, dialogue, and narration to tell the story of Clara and the Nutcracker. Crafts, cookies, cocoa, a performance, and a special meet and greet with the principal dancers! Read more.

Annual Holiday Train Show at CT River Museum 11/22 – 2/19/23,
10am – 5pm: Bring the whole family to this exhibit, created by train artist Steve Cryan, featuring more trains, new scenery, and lots of surprises in the fully operational 26-foot model train layout.

Santa Visits the Shoreline Trolley Museum Friday, 11/25 and weekends through 12/19: Take pix with Santa and a ride on a trolley.

Holiday Magic at Florence Griswold Museum, 11/25 – 12/31: This year’s celebration features new twists on the traditional décor. Imagine a fictional mantel-decorating contest in the Griswold boardinghouse between the historic Lyme Art Colony artists. Inspired by their paintings, they rummage through their studios as well as old trunks in Miss Florence’s attic for festive objets d’art and holiday decorations. Miss Florence announces the winner and awards ribbons on her birthday—Christmas Day! Three Fantasy Trees add bespoke sparkle in the historic house and in the Krieble Gallery, over 220 painted palettes, adorn four stunning Artist Trees. Find out more.

Ocean House Annual Tree Lighting Ceremony, 11/26, 5pm: Ignite the Christmas Spirit at Ocean House’s Annual Tree Lighting Ceremony and Christmas Village. Santa Claus will make his big arrival on a fire truck plus fireworks! Seasonal snacks, and a cash bar. Find out more.

Holiday Lighted Boat Parade & Santa Arrives by Tugboat in Mystic on 11/26:  Santa Claus is coming to town and so is Mystic’s Holiday Lighted Boat Parade in Historic Downtown Mystic. Thousands gather at the Mystic River Park to watch Santa arrive at 2 pm on a 60’ tugboat. Get the details.

Legacy Theater, Stony Creek presents A Christmas Carol, 11/30 – 12/11: Adapted and directed by Keely Baisden Knudsen, this story illuminates the journey of one Ebenezer Scrooge and his guided self-reflection amidst the Christmas season in 1800s England. Get tickets.

Madison Chamber’s Ladies Shopping Night in Madison 12/1, from 5 – 8pm: Specials and events at participating shops in Madison. Learn more.

Lantern Light Tours at Mystic Seaport, 12/2 – 12/17 on Fridays and Saturdays: Lantern Light Village is an outdoor, free-roaming experience designed to exemplify the differences between the modern and 19th century holiday seasons. Enjoy festive lighting displays, live music, horse and carriage rides, plus a visit from St. Nicolas, and so much more! Interact with the denizens of our 19th century village as they prepare for Christmas Eve and join them in their end of the year festivities. Visit Mystic Seaport for tickets.

Winter Wonder Day at Lyman Allyn Free First Saturday, 12/3, 11-3pm: Start your holiday season with a visit to Winter Wonder Day at the Lyman Allyn! Learn about different cultural holiday traditions, create great holiday crafts, contribute to a community artwork, explore the museum’s exhibitions, take your photo with Santa, and more! Visit the website.

Holidays at The Little Red Barn at Bishop’s Orchards, 12/3 & 12/4 and 12/10 & 12/11 from 10am to 4pm: The Bishop’s Orchards Little Red Bar[n] will be turning into Santa’s Workshop. Enjoy two weekends on the farm, filled with cookie decorating, ornament making and a special visit from Santa himself! Kids tickets will include all activities, as well as free candid photos with Santa. The Wine Barn will be serving adult beverages, snacks and hot drinks. Make an afternoon of it and purchase a s’mores kit to enjoy a special treat at one of our bonfires. Shop around the Little Red Barn for home goods and seasonal favorites! Get tickets.

Christmas in the Village, Goodspeed Airport, 12/6 at 5pm: Santa will fly into the airport and visit in East Haddam Village. Find out more.

Deck the Walls at Lyme Art Association, 11/18 – 1/1/2023: Juried exhibit of Lyme Art Association members. This exhibit of well-priced artworks is perfect for gifting! Find out more.

Opera CT Presents ‘Amahl and the Night Visitors’ 12/10 at 2pm at Hill-Stead’s Makeshift Theater. See details.

2022 Holiday Events & Promotions at The Shops at Yale, New Haven Tree Lighting, Holiday Village, Storytelling with Santa, Ice-Carving Competition, Strolling Carolers, Small Biz Pop-Up and more during the season. See all the events. 

The Nutcracker at The Garde, 12/10 – 12/11: Get tickets to see this holiday favorite performed by Eastern CT Ballet with dancers from the New York City Ballet at The Garde. Get tickets!

Niantic Light Parade, 12/10 from 6 – 9pm: New Englands largest and brightest light parade! Check the website for updates and details.

Breakfast with Santa at Madison Beach Hotel, 12/11 from 9 – 11am: Photo op with Santa, mimosas for the grownups and treats for the kids plus a scrumptious breakfast. Visit Madison Beach Hotel.

Holiday Party at Smith Farm Gardens:  12/17, 7-10pm Come for some holiday cheer in the festively decorated farmhouse. Hors d’oeuvres provided throughout the evening with cash bar. Live holiday music begins the celebration, with a DJ and dancing to follow in the Great Room. Learn more.

Hip Hop Nutcracker at The Shubert, New Haven, 12/30, 7pm: A holiday mash-up for the whole family!  Directed and choreographed by Jennifer Weber, this contemporary dance spectacle is a re-mixed and re-imagined version of the classic, smashing hip hop dance and Tchaikovksy’s timeless music together into a heart-stirring and inspirational holiday event. Get tickets.

Holiday Lights at Olde Mistick Village, 11/18 – 1/2023: The Holiday Lights Spectacular returns to Olde Mistick Village with the largest holiday light display in southern New England. Over a half-million lights will decorate the Olde Mystic Village square of shops and restaurants for families and holiday enthusiasts to enjoy. See more.

Stroll the Shoreline:

Holiday strolls in Shoreline villages feature Santa visits, sleigh rides, caroling, tree lightings and special events in the shops. Here are some dates:

Niantic Holiday Stroll on 11/26 from 3 – 7pm: Enjoy store specials, sales and giveaways while shopping local this Small Business Saturday from 11am to 7pm. Stop by the Food Truck court to warm up with delicious bites. Go on the hunt for some mischievous elves in the shop windows with our Mermaid Elf Trail. (We hear they’ve dressed as mermaids to help blend in.) Stay tuned for details.

Madison Small Business Saturday and Santa Comes to Town on 11/26, 10-6:30pm: Small business Saturday comes to Madison the Saturday following Thanksgiving. Come down and stroll the shops see what they have to offer this holiday season!! Santa arrives at Noon riding down Main Street to the steps of Cafe Allegre, where he will listen to all the boys and girls holiday wishes. Find out more.

Mystic Lighted Boat Parade on 11/26, 6:15pm: The 19th Annual Mystic Holiday Lighted Boat Parade will take place on the Saturday after Thanksgiving. Following Santa arriving by tugboat and the lighting of the Mystic River Park Christmas tree, spectators flood both sides of the Mystic River to see the decorated and decked out boats pass by. Decorated vessels will parade down the Mystic River just after 6pm and return to the Mystic River Park, where spectators and judges will be gathered. Learn more.

New Haven Tree Lighting & Holiday Village on 12/1, 5:30pm: Join the Elm City as they kick off the holiday season with their official Tree Lighting Ceremony & Holiday Village on the New Haven Green. The Tree Lighting Ceremony will feature entertainment, photo opportunities with Santa & Mrs. Claus, and many more surprises for the whole family! This event is family-friendly, and pet-friendly with retail products by local entrepreneurs perfect for holiday gifts. The Holiday Village runs through the weekend. Details here. 

First Friday in Chester and Starry Nights on 12/2, 5 – 8pm: Join the Merchants of Chester for an extra special First Friday celebration! In addition to new exhibitions, seasonal menus & ice cream flavors, live music and great shopping, Christopher Owens’ STAR installation (& wishing booth) will be lit, all at once at 5:45pm!  Come out to Main Street for this exciting event and stay for shopping and dinner. Visit the Chester website. Purchase a star!

Stonington Lobster Trap Tree at Stonington Town Dock lighting at 4:30 on 11/26: Lit from 4:30 to 10pm through end of January. See more.

Old Saybrook Starlight Festival on 12/3: Centered on the Town Green, this day-long family friendly event will have you feeling merry & bright! Activities include: Meet with Santa, the Frosty 5k, a Stocking Walk, Giving Tree, Story Time, Ornament Decorating Workshop, dance performances and more. Get details.

The Deep River Annual Holiday Stroll and Holiday Light Parade on 12/3, 4-7pm: Visit local merchants for festive cheer and specials. Festivities include CT Yuletide Carolers, DR Historical Society’s Festival of Trees, Tree Lighting, Visit from Santa, Gingerbread House Contest, Fire Performer and Inflatable Snow Globe and more. Find out more.

Stonington Village Holiday Stroll on 12/3, 5:30pm: Every year, on the first Friday evening in December, the Stonington Village Improvement Association (SVIA) sponsors a tree lighting ceremony in Wadawanuck Square that includes a community carol sing and a special visit by Santa. Immediately following the lighting of the tree is the annual holiday stroll down Water Street, which will be closed from High Street to Cannon Square. Merchants keep their shops open late and welcome visitors. The shops compete for the title of “Best Dressed Holiday Window” in the annual Borough A-Glow contest. Get the details.

Groton Holiday Kickoff on 12/3, 5 – 7pm: Groton’s Holiday Kickoff Celebration is an event that incorporates all holidays celebrations and traditions; Christmas, Hanukkah, Kwanzaa, Three King’s Day as well as other holiday traditions. There will be displays of all holiday celebrations, children’s activities, a bell choir, carolers, holiday dancers, hayrides and food trucks! Plus special guest, SANTA!! See more. 

Westbrook Holiday Parade and Tree Lighting on 12/4, 5-6pm: Join the fun on this annual Holiday Parade and Tree Lighting including Santa and Mrs. Claus, Ice Carving, Crafts and reindeer food, S’mores at the bonfire, Horse-drawn carriage rides and much more abundant good cheer. Get the details. 

Downtown Mystic Holiday Stroll & Luminaria on 12/6 at 6pm: Stroll the festive streets of Historic Downtown Mystic and listen to the carolers rejoice in the holiday spirit as Santa makes his way through the hustle and bustle! Merchants will keep their shops open late so everyone can get a head start on their holiday shopping while enjoying hot cider, cookies and other goodies in the stores. This is a community event, free of charge and open to the public. Read more. 

Niantic/East Lyme Light Parade on 12/10 at 6-9pm: SAVE THE DATE for New England’s largest and brightest Holiday Light Parade. The 2022 Niantic Light Parade will be held on Saturday night December 10th on Main Street Niantic beginning at 6 pm. More details here.

Ivoryton Illuminations, throughout December: Visit the brightest village in Connecticut throughout December as Ivoryton lights up with over 400,000 lights!  Tune your radio to 101.5FM listen to holiday music. Sponsored by the Ivoryton Village Alliance. Visit the FB page.

Decoration and Inspiration:

Looking for a little inspiration for decking the halls? Here are some favorite shops for everything from decorations to ribbons to greens.

Saybrook Home (formerly Saybrook Country Barn) is a feast of inspiration for the holidays, with room after room of ornaments, trees, swags, centerpieces, candles and gifts.

Madison Flower Shop, for trees, swags, greenery, centerpieces and an enormous selection of ribbons and ornaments.

R.J. Vickers Herbery, Chester for handmade, one-of-a-kind wreaths, topiary, ribbon and dried herbs and flowers.

Mar Floral‘s long-lasting arrangements are far from ordinary.