‘Tis the season for merriment and festivity, and if there’s one thing Richmond does well, it’s decking the halls. From pop-up markets to tacky lights extravaganzas, boat parades, and Santa visits, there’s no shortage of festive ways to kick off the season. Read on for a few we’re looking forward to this year that allow us to get in the holiday spirit while checking a few names off of our list!


Santa’s Cocktail Shop and Mystic Markets Holiday Sip and Shop

Thursday, December 8, 5-9pm, December 17, 1-6pm

Cirrus Vodka

Check out Santa’s Cocktail Shop of merry drinks at Cirrus Vodka featuring four holiday-themed drinks while shopping at Mystic Markets’ Holiday Sip and Shop. The shopping event is limited to select dates, but Santa’s Cocktail Shop will be popping up Thursday-Sunday through January 1.


Breakfast with Santa and a Trolley Ride

Saturday, December 10, 8-10am

Westwood Fountain

Kick off the holiday season by visiting the jolly man himself before strolling the avenues shopping in the extensive collection of locally-owned businesses found along Libbie, Grove, and Patterson Avenues.


Winter Wander

Sunday, December 11, 12-4pm

The Valentine and Court End Neighborhood

Enjoy free holiday festivities in Court End, including carriage rides, live music, crafts, inflatables, and complimentary admission to historic sites. Be sure to visit The Valentine’s gift shop for some of the best Richmond-centric gift ideas in town.


A Holiday Boutique

Daily through December 23, 10am-6pm

Diversity Thrift

Looking for more sustainable holiday gifts this year? Keep sustainability front and center when shopping Diversity Thrift’s Holiday Boutique featuring the best vintage wares, art, antiques, silver, fine china, estate jewelry, vintage clothing, ceramics, rare books, rugs, vintage toys, and more that have been saved throughout the year for this special shopping event.


The Winter Market

Daily through December 24, 11am-5pm

Studio Two Three

Find the perfect one-of-a-kind gift during this pop-up holiday market featuring hundreds of works by local artists.