Cozy Up to Winter Dining

A tabletop fire keeps diners warm on the patio at Smashing Grapes in Annapolis.

By Krista Pfunder 

A few years ago, I visited Montreal during the fall. Bundled up for temperatures that felt more like winter to a native Marylander, I discovered that restaurants had outdoor spaces for diners, complete with tents and heaters.  

The atmosphere was romantic, charming and reminiscent of a winter wonderland. 

Fast forward to November 2020, when COVID-19 cases are back on the rise, and many restaurants in our area are recreating that picturesque French Canadian scene, complete with tents, heaters, blankets and fires. 

Restaurant owners want to extend the outdoor dining season as long as possible for their customers. 

“Most of our customers are very good about being compliant with guidelines, and that includes preferring eating outdoors over indoors,” says Jan Travers, co-owner of Westlawn Inn in North Beach ( “Some bring blankets, two jackets and come a little earlier than they usually dine.” 

And in an effort to keep the added outdoor space, local food establishments are transitioning their outdoor dining areas for fall and winter. 

Diners bundle up on the porch of Westlawn Inn in North Beach.

“Many of the restaurants in downtown Annapolis are putting up tents for the winter for those that prefer to dine outdoors,” says Erik Evans with the Downtown Annapolis Partnership. “The tents will be heated, have socially distanced tables and plenty of air circulation.”  

As the cooler weather arrives, five restaurants in downtown Annapolis: Federal House, McGarvey’s, Middleton Tavern, Market House and Iron Rooster— referred to by their respective owners as the Market Space restaurants—are among those adding tents. 

The five restaurants used the roadway next to the restaurants to accommodate outdoor diners when the city allowed them to use street space after the pandemic hit.  

“We will have five separate tents with sides to separate the stores,” says Jeremy Black, owner of Federal House. “I’ve left the covering off this weekend since it’s supposed to be nice out. My tent goes up on Monday. I’ll put two sides of the tent up—those between Iron Rooster and Market House—but will leave the other two sides off until nature decided they need to go up.” 

An outdoor firepit beckons to patrons at JesseJays Latin Kitchen in Churchton.

Other restaurants are doing their best to keep diners comfortable, even without tents. The Westlawn Inn restaurant features a large wrap-around porch that they plan on keeping open as an option for diners. 

“The porch will be open for fall and winter,” Travers says. “If people want to sit outside, they can. We have a couple of space heaters and blankets we are offering,” Travers says. 

Newly opened Smashing Grapes in Annapolis features a large outdoor patio area popular with customers. “We have heaters and firepits,” says restaurateur James King of Smashing Grapes. “Many of our patrons are still utilizing our outdoor dining area on a daily basis.” 

At Skipper’s Pier in Deale, the semi-open air atrium dining area boasts a fireplace to keep customers warm. “Trust that we are providing a safe—and cozy—place for you to dine,” Skipper’s Pier co-owner Jessica Rosage says. 

Transition Isn’t Without Challenges  

The unexpected demand for space heaters and tents has made acquiring them difficult for area restaurants. 

“It’s been quite the struggle to find space heaters,” Travers says. She checked online at a local Home Depot as the number of available units quickly dropped while her husband, co-owner Lee Travers, was en route to purchase them. 

The North Beach restaurant ended up being able to purchase two table-top size heaters. 

“We have had no issues finding space heaters,” Smashing Grapes’ King says. “But what we have found is that they are taking longer to ship than usual.” 

Federal House experienced the same. The heaters for the downtown restaurant are not expected to arrive until November 16.  

“I ordered them in early September,” Black says. It took Black five weeks to get a tent. But he considers himself lucky to have found one at all. “Some restaurants have been forced to rent tents,” Black says. 

Also challenging is planning for the future and yet-to-be-determined diner demand. “We have no data to go by,” Black says. The downtown restaurant—which is fully booked for Saturday—points out that this experience is new. “We don’t yet know how to handle it,” Black says. 

Not all restaurants are experiencing the same popularity the Federal House is seeing. “As the temperatures have been dropping, we have noticed a drop in diners; especially at night,” says Jayleen Fonseca, co-owner of JesseJays in Churchton. “Our dinner service ends quicker and earlier than before. With the expected surge in cases, I believe we may be required to go back to carry-out only again. These are definitely uncertain and uneasy times.” 

“Our sales have dropped a lot,” Skippers Pier’s Rosage says. “We need local support to get through the winter.” 

Another challenge is keeping up with ever-changing guidelines and rules—and getting answers from overwhelmed health departments. “Guidelines can be very subjective and the health department (particularly to restaurants) has not been good at returning calls when messages are left,” Rosage says. 

“I’ve told my staff to expect that it will almost be like we’re back in May,” Black says. “Most likely guidelines will change almost daily.” 

State Assistance 

Governor Hogan recently announced additional COVID-19 relief programs for restaurants. The state will give out a total of $50 million across each county and Baltimore City, based on the number of restaurants in the area. Anne Arundel County will receive just over $5 million and Calvert will receive $646,295. 

Anne Arundel County is matching the state’s offer, committing $5 million of its federal funding to the grant program, bringing the total available to restaurants to $10 million. Anne Arundel County businesses can use the grants to cover operating expenses like rent, payroll and utilities, personal protective equipment, cleaning, and buildingtheir online presence.   

The application period for the Anne Arundel County grants is expected to open in mid-November. 

Calvert County began disbursing funds from the grant program Nov. 9 and will continue through Dec. 11, or until all funds are expended. Small restaurants (with one to seven employees) may receive $10,000 and larger restaurants — (with eight or more full-time employees) may receive $15,000. 

These funds may be used for rent, payroll or buying equipment to expand outdoor dining, such as tents or heaters. 

As for the heaters that Federal House is still waiting on, they are industrial-grade and generate heat for 1,500-2,000 square feet. The large heaters will sit outside of the tents and diffuse the air underneath, helping to keep air flowing. 

To my delight, Black says that the name of the outdoor area will be Federal House Winter Wonderland—complete with hanging snowflakes. 

Diners in Market Space in Downtown Annapolis.