Gloucester’s Holiday Season Retail Therapy 

November 15, 2023 / Things to Do & See

Holiday shopping can be difficult to enjoy if you find yourself browsing at chaotic and busy malls or overcrowded box stores. Wouldn’t it be great if we could enjoy holiday shopping like our grandparents did? Strolling along quaint downtown streets browsing in windows, delighting in twinkling lights and listening to festive music while we find our treasures to gift. 

As we gear up for the holiday season, Gloucester merchants and the Gloucester Downtown Association hope to create an idyllic scene for visitors and locals to savor by transforming the streets of downtown into a winter wonderland of lights and decorations, not to mention, phenomenal deals! 

During the weeks between Thanksgiving and Christmas, small businesses in Gloucester hope to create the ideal environment and offer fantastic deals to entice visitors to become patrons of their establishments and enjoy a little retail therapy in the days leading up to Christmas. 

Here are some of the events you and your family may want to participate in as you “deck the halls” and prepare for the giving season. 

Shop LocalBlack Friday & Small Business Saturday 

For many shoppers, the day after (and the weekend of) Thanksgiving marks the true beginning of the holiday shopping season. Black Friday has historically signaled the start of the holiday season with blockbuster deals for customers willing to embrace the idea of getting out early and enjoying the festivities of shopping. 

The shops and merchants of Gloucester’s historical downtown offer some amazing deals and hope to encourage shopping by opening early and extending hours this holiday weekend. 

Small Business Saturday offers the perfect opportunity for small businesses to increase sales and for shoppers to find unbelievable bargains on gifts and services. Gloucester in particular finds this day to be a great chance to encourage local shopping in our many small businesses that depend on customers year-round. 

To promote shopping downtown during this busy weekend, Gloucester merchants pull out all the stops by decorating shops with festive window displays and twinkling lights. This creates a traditional holiday experience for shoppers that malls and box stores can not beat. Additionally, holiday events drive visitors to the area such as the Gloucester Christmas Parade, Middle Street Walk, Annual Tree Lighting, and Gloucester’s famous Lobster Trap Tree that attract people from far and wide. 

If you and your family love to experience a genuine holiday shopping trip complete with hot cocoa, strolling carolers and music, Gloucester has everything you need to kick off your holiday shopping. 


Annual Gloucester Ladies Night – All Day 

Shopping is more fun if you do it with a friend, and what’s better than shopping with your gal pals in Gloucester on the Annual Ladies’ Night? 

What was once a nighttime event has expanded into an all-day event encouraging the ladies to get their shopping done while enjoying holiday music, viewing the Lobster Trap Tree and maybe even enjoying a beverage or two. 

Ladies’ Night in Gloucester is held annually and is in its 49th year! This day and night is not only a great opportunity to get some shopping done for handmade, unique, and one-of-a-kind gifts to be found in shops in downtown Gloucester but also a chance to share the experience with girlfriends or family members. 

This year’s Ladies’ Night – All Day is being held on December 7, 2023, from 10:00 a.m. to 10:00 p.m., with specials and activities offered at shops up and down Main Street.

Gloucester’s Middle Street Walk 

This time-honored event is a must-attend for those looking to get in the spirit of the season. Free events all day along Middle Street and beyond include bell ringers, wreaths and greenery sales, trolley rides, live music and concerts, baked goods, Gingerbread Houses, sing-a-longs, performances and so much more! 

The Middle Street Walk Committee has planned quite the walk for the 25th year and hopes to see you there. The events start at 10 am on December 9th and go on until the Lobster Pot Tree Lighting at 5 pm. 

Annual Gloucester Men’s Night – All Day 

Being held this year on December 14th, Gloucester’s 45th Annual Men’s Night is similar in the festivities to the Ladies’ Night, except this time the treats and specials are geared toward the men doing the shopping.

Grab your best buddies and head down to Main Street in Gloucester to enjoy some free treats, tastes of the season, and some wallet-busting bargains! 

Gloucester has so much to offer this holiday season from the traditional experience of strolling to the sounds of carolers to finding that perfect gift for the hard-to-buy for a relative. Join us downtown and support our small businesses that make this time of year so special for locals and visitors alike.