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A Look at Christmas Strolls in Southern Connecticut and Rhode Island in 2018

With Thanksgiving behind us, it’s hard to believe that we’re heading into the Christmas season. Luckily for residents of South County, Rhode Island and New London County, Connecticut, you’ll have plenty of chances to get into the holiday spirit through the various Christmas strolls in the region.

Generally, Christmas strolls provide a day for businesses in the downtown core to stay open late and give residents plenty of reasons to head into these areas for the evening. In addition, since your kids will be entertained by the extracurriculars going on, you won’t have to worry about them complaining while you try to get your shopping done.

Make sure you mark a few of the local holiday strolls on your calendar in the weeks leading up to Christmas, as they will ensure that you immerse yourself in the holiday spirit this year.

Block Island’s Holiday Shopping Stroll Weekend

For the 28th year in a row, Block Island will host its Annual Holiday Stroll between November 23 and 25. This event gives you the chance to get out of town for a day or two over Thanksgiving Weekend and find some great deals in the process. Local retailers are open from 10:00 AM – 5:00 PM on all three days and New Shoreham is all decked out in festive decor, including the famous Lobster Pot Tree.

There will also be a raffle draw on Sunday, November 25, which you'll have to collect stamps from stores around town to enter. You can catch the high-speed ferry to Block Island from Narragansett, with two sailings departing each way per day.

15th Annual Niantic Main Street Holiday Stroll

Thanksgiving Weekend hosts the 15th Annual Niantic Main Street Holiday Stroll, as well. On Saturday, November 24, head down to Niantic Main Street for a family-friendly day of activities, including horse-drawn carriage rides, holiday music, a chili cook-off, a s'more station, and complimentary hot chocolate and cider. For the kids, there will also be crafts, games, and arts, in addition to Santa Claus arriving on a red fire truck.

Of course, the event is centered on the downtown shopping scene, and many restaurants and shops will have specials throughout the evening. There will be the Snowflake Drop, as well, which will provide further discounts at select shops. Everything gets started at 3:00 PM and runs until 7:00 PM, with the Christmas tree lighting taking place at 5:00.

Holiday Stroll at the American Velvet Mill

A third Thanksgiving Weekend stroll is held at American Velvet Mill, a mall in a historic building in Stonington, on Saturday, November 24. This year's stroll will celebrate the mall's 130th anniversary and will bring craft, food, and drink vendors to the building between 3:00 and 9:00 PM. There will also be live entertainment, activities for the kids, and a visit by Santa Claus himself, so make sure you come by and support some small local businesses along Connecticut's coast.

Wickford Festival of Lights

There's a four-day event in Wickford Village between November 29 and December 2 called the Wickford Festival of Lights, and it includes a holiday stroll. Throughout this event, shops are open on Brown Street and Main Street until 9:00 PM and the entire area is illuminated with Wickford Festival of Lights North Kingstown, RI.thousands of white lights, turning Wickford Village into a winter wonderland.

Heading to Wickford Village that weekend also means you can take a hayride with Santa after he arrives at the town dock on a boat, witness the tree lighting, or experience the Elf Parade. The Wickford Festival of Lights is fun for the entire family, and since it's four days long, you'll have plenty of opportunities to get there to check it out.

Holiday Stroll and Luminaria Mystic

Not all of these holiday strolls are on the weekends, as Tuesday, December 4 brings the Holiday Stroll and Luminaria to Mystic. Head to downtown Mystic between 6:00 and 9:00 PM and take part in this annual tradition, which includes plenty of discounts and specials at local shops, a visit by Santa, gift wrapping at the Mystic Museum of Art, and performances by local pirate troupe Free Men of the Sea.

As you wander the area, you'll notice that hundreds of luminaria line the streets and Mystic River Park, and you'll also have the chance to see performances by Saxophone Santa, the Noank-Mystic Community Band, the Mystic River Chorale, and other local choirs.

22nd Annual Downtown Stroll and Luminaria in Westerly

The very next night, Wednesday, December 5, Westerly will host its 22nd Annual Downtown Stroll and Luminaria. The festivities get started at 5:00 PM and run until 9:00, with luminaries lining the sidewalks and local stores providing discounts and special promotions. You'll find complimentary hot chocolate to keep you warm and cookies for a snack as you shop and support the region's merchants.

In addition to the shopping, this event offers a hayride with Santa, and wandering carolers provide ambiance throughout the evening. The stroll even extends across the bridge into Pawcatuck, Connecticut, should you have interest in doing some shopping there.

Holiday Stroll in the Boro!

There's a holiday stroll in Stonington Borough on December 7 that runs right through the heart of town on Water Street. The event runs from 5:00 – 9:00 PM and businesses throughout the area stay open late to accommodate shoppers. These shops provide snacks and drinks as you stroll, as well.Stonington Boro Holiday Stroll 2018.

As you shop, you'll see Santa riding his motorcycle up and down the street, in addition to Christmas carolers singing your favorite holiday tunes as the town's Christmas tree at Wadawanuck Square lights up for the first time this season.

Wakefield Winter Wonderland

For the third year in the row, the Wakefield Winter Wonderland will come to the village on Saturday, December 8. Everything gets started at 5:00 PM with a holiday parade at Wakefield Elementary School, followed by the lighting of the Christmas tree and carols at The Contemporary Theater Company.

From there, the entire family can stroll along Main Street, participating in a scavenger hunt put on by local businesses and hopping on the South County Trolley for a ride. Merchants along Main Street will be dressed up as their favorite characters from holiday-themed movies, so you never know who you'll see during your night in Wakefield Village. The event runs until 11:30 PM, giving you plenty of time to explore.

Plenty to Do All Season Long

As you may have noticed, there’s a holiday stroll taking place every weekend between Thanksgiving and the middle of December in southern Rhode Island and Connecticut, with additional strolls coming during the week. Whether you want to head to Block Island for a couple of days to check out some shops or go somewhere close to home for an evening, the entire coastal area is full of Christmas activities for the next month.

Get out there and experience the festive season as much as possible and don’t forget to support local merchants during the 2018 Christmas strolls.