Scenic Shopping Holiday Events with Spotlight on Shops, 2021

Central St., downtown Wellesley, Mass. during December

Carol Lee's Cottage, Bearskin Neck, Rockport, Mass.

Yes Gallery at Christmastime, Brown St., Wickford, R.I.

Hayrides with Santa, Festival of Lights, Wickford, R.I.

Although pandemic restrictions are in place, Scenic Shopping towns are forging ahead determined to have a joyful and busy holiday shopping season. Many annual traditions have resumed and they are outdoors anyway so visitors and locals are excited to participate after being disappointed last year. Here are some December events, with an emphasis on discounts and special festivities offered in small shops. Kicking off the list is the Annual Marblehead Christmas Walk and Holiday Stroll on Dec. 2-5, 2021. An artisan market plus lots of special events are taking place, in addition to the Tree Lighting on Friday night, and the Arrival of Santa on Saturday. (More)

Santa and Mrs. Claus greeting visitors outside Mud Puddle Toys, Pleasant St., Marblehead, Mass.

Shops in downtown Marblehead are decorated, and merchants offer refreshments for shoppers. Santa and Mrs. Claus enjoy greeting visitors in front of Mud Puddle Toys on Pleasant Street.

On December 2-5, 2021, the town of Wickford in Rhode Island holds their Festival of Lights weekend with the arrival of Santa, hayrides, and an Elf Parade. On Sunday, you can see "The Ladies of the Rolling Pin", a Border Morris dance team performing traditional English folk dance right in the village. Most shops stay open late. See our Wickford page for a list of shops in this town.

This year, Rockport, Mass. is holding events all month long and into the New Year. Rockport's many Christmas traditions are back, including Santa's arrival by boat, the tree lighting and the Christmas Pageant. The town's special shopping nights this year are Dec. 3, 10 and 17 when shops are open until 8 p.m. Their shopping nights have themes: Dec. 3 is Be Festive, Dec. 10 is a gift drive and Dec. 17 is ugly sweater night. See their webpage, Christmas in Rockport for more information.

The Wellesley Square Holiday Stroll on Sunday, December 5, 2021 this year is a special shopping event along with holiday fanfare such as carolers, a tree lighting, photos with Santa, a scavenger hunt and the chance to meet Frosty and Rudolph throughout the day. The stroll is from noon to 6:00, and street parking is free in December.

In Kennebunkport, Maine, the Annual Christmas Prelude turns the whole town into a magical New England setting with special events, including craft fairs, live entertainment, warm beverages and loads more from December 2-12, 2021. See their website for the schedule and a guide for visitors.

The Boothbay Lights celebration takes place in Boothbay and Boothbay Harbor, Maine through Dec. 19th, 2021. In Wiscasset, Maine the Wiscasset Holiday Marketfest is being held Dec. 3-5, 2021. The shop owners in Wiscasset, along with a pop up Holiday Gift Shop of artists' creations are looking forward to assisting you with your holiday shopping. Wiscasset is also home to art galleries and antique shops.

On the island of Nantucket, the Annual Christmas Stroll is taking place Dec. 3-5, 2021 with many festivities such as Santa's Village, a Christmas Market, Santa's arrival by boat, carolers, storefront Christmas decorations, and local performances.

From December 9-12, 2021 the town of Edgartown on Martha's Vineyard holds an action packed long weekend of family friendly activities, Christmas in Edgartown. Edgartown shops compete in a window decorating contest, offer discounts and complimentary beverages. Fund raisers for local charities are combined with sales and raffles. Kids can participate in a scavenger hunt, write a letter to Santa, work on coloring pages and decorate cookies. The Edgartown Lighthouse will be lit up on Friday night, and Santa will be in the parade on Saturday.

On December 10 through 12, 2021 Chatham, Mass. on Cape Cod is holding their Christmas Stroll weekend. This celebration features local shops and lots of Christmas cheer. Carolers, horse drawn carriage rides, Santa's arrival, the tree lighting, and entertainment are all part of the festivities. Shops hold promotionals like special sales, raffles and complimentary beverages.

In Hingham, Mass., holiday festivities are called Holly Jolly Hingham. There will be horse drawn hayrides on Saturdays (Dec. 8, 11, and 18, 2021) while shops stay open on weekends for extended hours. Stores also stay open late, until 7 p.m. on Dec. 16 for Third Thursday Strolls which includes live music and historical tours. In nearby Cohasset, the town hosts Cohasset Village Holiday Stroll at Cohasset Commons on Dec. 11 from 4-7 p.m. Santa will stop by on the town fire truck, and shops will have special activities like cookie decorating and ornament making.

The pandemic is still with us so check the CDC (Centers for Disease Control) for details on Covid guidelines. Research local guidelines in the state and town of your destination. Shops follow Covid protocols in their area. With many events being held outdoors, and observance of Covid recommendations and requirements, the holidays can be somewhat back to normal and we can support the small shops in these picturesque villages and towns.

See our Scenic Shopping webpages for more details on shop names, restaurants, places to stay, and activities in Marblehead, Wickford, Rockport, Wellesley, Kennebunkport, Boothbay Harbor, Wiscasset, Nantucket, Edgartown, Chatham, Hingham and Cohasset.