The Connecticut River valley will be a great place to get into the holiday spirit this weekend, with festivities scheduled in Chester and Essex offering a chance to celebrate good cheer with friends and family.

On Friday, Dec. 6, Chester will once again come alive for a special holiday First Friday celebration with the lighting of the Christmas tree and menorah and holiday carols sung outside the downtown shops and restaurants until 8 p.m. Festivities start in front of The French Hen at 6 p.m. Santa is scheduled to arrive at 6:30 p.m.

Attractions include The French Hen’s elves serving up their holiday cocktail the “White Christmas” and the Chester Gallery showcasing its annual Postcard Show. At Lark, artist Rachel Carlson will unveil a new body of small works painted on New York City Metrocards. Kismet Chester will display owner and jewelry designer Gillian Davis’s Glitter & Gold Collection along with a pop-up sale and visitors are encouraged to sip sparkling wine and peruse sale items all weekend long at the-e-list.com shop.

Kids can enjoy free hot chocolate and cookies with any of the kids’ meals at The Pattaconk 1850 Bar & Grille on First Friday, and they can also send a letter directly to Santa from one of the Santa mailboxes on site. )There will be some spiked eggnog for adults, too.)

The musicians of Arrowhead and Friends will perform for shoppers enjoying with a glass of holiday cheer while surveying the t paintings of artist Leif Nilsson at the Leif Nilsson Spring Street Studio and Gallery. The evening also marks the last chance to tap Caryn Paradis, LLC Interior Design for free design tips as part of its Ask the Designer workshop.

Elsewhere around Chester, shops will be open until 8 p.m., with most offering complimentary snacks or beverages.

Also running from 5 to 9 p.m. there will the annual Chester Holiday Extravaganza at the Chester Meeting House, 4 Liberty Street, which will feature a wide array of goods from local artisans as well as live music and food. This year, goods will include handmade soy candles, nature inspired jewelry, handmade felted ornaments, all-natural cleaning products, back packs, pouches, totes, and more.

“This is just another way that the Chester community comes together to celebrate our town, our merchants, and our residents,” said First Selectman Lauren Gister. “Chester is a fun town and this is a night when everyone can come and experience our fun and excitement.”

Lots to Do in Essex

Over in Essex, on Saturday, Dec. 7, there are a bevy of festivities planned including the bi-annual Essex Auxiliary Holiday House tour, the village Holiday Stroll, and the Ivoryton Illuminations.

“We have so much going on town, there is something for everyone to enjoy,” said First Selectman Norm Needleman.

Seven homes in the village of Essex will be decorated with festive arrangements for the Holiday House Tour (see “Time for the Bi-Annual Holiday House Tour in Essex” on page 5). In addition, there will be a Holiday Boutique at the Town Hall at 29 West Avenue. Tickets for the tour are $40 the day the event and will be sold at the Town Hall.

From 1 to 4 p.m. the village of Essex will once again be transformed into a winter wonderland as the Essex Board of Trade celebrates the 25th anniversary of the Essex Holiday Stroll complete with old-fashioned, horse-drawn wagon rides with Santa from 1 to 3 p.m.; food trucks; a Santa letter drop at the town gazebo; pictures with Santa at the gazebo from 3 to 5 p.m.; church bells will be chiming; and boy scouts selling holiday ornaments.

In addition, specialty shops throughout town will offer stroll specials, restaurants will feature festive dining menus, and streetscape luminaires will light the way for an end of the day stroll to visit the Griswold Inn’s Christmas tree in Griswold Square.

Happening the same day from 5 to 8 p.m. the epic Ivoryton Illuminations will light up the brightest town center for the 10th year in a row.

What started as a conversation between friends has grown into the third-largest holiday light show in the state, something for which the village of Ivoryton is very proud.

“Honestly, we never thought it would get this big or last this long,” said event founder Chris Shane. “Our first year we had 100,000 lights; last year we had 500,000. It really is something.”

A lot of work goes into the planning and execution of the ornate display.

“We start working on it in October, getting the lights out of storage, testing them all and ordering what we need,” said Shane.

A key attraction of the evening is the lighting of the big tree at 6 p.m. and the aerial arrival of Santa in his sleigh (courtesy of some volunteers operating construction equipment). In addition, unwrapped toys that are donated to the Ivoryton Library during the month of November are given out by Santa Claus, who also meets with children to hear their Christmas wishes, pose for free photos, and give out special gifts and candy canes.

“This is really why we do all this, to see the children smile,” said Shane.

Also part of the event, there is an elf hunt, carol singing, a Holiday Bazaar, hot chocolate and mulled cider, the Lion’s Club hot dogs and hamburgers, cookie decorating, live music, a petting zoo, and an opportunity to write a letter to Santa and soldiers serving far away.

“Every year this event gets bigger and better and the community looks forward to the opportunity to come together, to celebrate the holidays, in the beautiful village of Ivoryton,” said Needleman.