If you want to grab a macchiato during a gale, Oscar’s Coffee is your best bet.
Tucked in a converted 1972 Shasta camper on the very edge of the Chesapeake Bay, the outdoor spot is open year-round regardless of the weather.
“We’ve worked in pretty bad weather,” said Elle Bachkosky, one of two baristas working the shop on a day when the wind was gusting at 25 mph. “The rain doesn’t scare people away.”
For a small city, Annapolis has a double shot of coffee shops. Just about every part of town has a place of its own, even if some of them are chains like Starbucks, Dunkin’ and, most recently, Tatte Bakery & Cafe.
A good coffee shop is about good coffee and tea, nice noshes to go along with them and something equally essential but a bit harder to define — a functional third space beyond home and office.
Oscar’s is a neighborhood place, hard to find and harder to drive to unless you really want a flat white at a spot overlooking a sailboat-filled marina, the Severn River and the Erector-set outline of the Bay Bridge on the horizon.

“Sometimes we know the dogs’ names better than the people’s names,” Bachkosky said.
The same sense of familiarity can be found at 49 West Coffeehouse, located in a little knot of caffeine just a few steps from the State House. It’s across the street from a Dunkin’ and a few doors down from Cafe Ole, a hole-in-the-wall that’s a great pop-in shop.
49 West offers a more substantial setting, almost crossing into a restaurant and music venue. But it manages to maintain the coffee shop vibe, and after 30 years, it is a frequent meet-up spot for city, county and state government figures.
Many of the coffee shops in Annapolis serve Ceremony Coffee, the only roaster in Annapolis.

Inside its shop at 90 Russell St., there’s an industrial decor that suits the purpose of the building, and a handful of benches and tables offer you a latte as close as you can get to fresh roasted.
A few more tables are located outside, but the real star may be the racks of freshly ground coffee in a variety of blends.
Other essential coffee shops in Annapolis include:
Rise Up. With two locations, one across from Annapolis Town Center and the other at City Dock, this regional chain brews up coffee from its roastery in Easton.
Bean Rush Cafe. Located in an old home, the West Annapolis location is popular with residents of one of the out-of-the-way neighborhoods. Other locations are in Crownsville and Glen Burnie.
The Big Bean. The third location of a Severna Park tradition, this shop is on the site of the 2018 Capital Gazette mass shooting. The owners believe in the power of coffee to heal.
Bitty & Beau’s. Coffee at City Dock with a purpose, the national chain offers employment opportunities for people with intellectual and developmental disabilities.
Curate. Beautiful pastries combined with good coffee in a modern building on the buzzy section of West Street. What’s not to like?
Old Fox Books & Coffeehouse. A mix of two passions for many people, coffee and books. The Maryland Avenue location is a plus, too.
1845 Coffee: The date tells the story, the Naval Academy’s founding year. Tucked just inside Gate 3, you don’t have to go through security for a Americano.
InGrano Bistro Bakery. The farthest-out Annapolis option, but the pastries, while expensive, are worth the drive.
Here are some other great things to do in the week through Nov. 26.
Great Annapolis Gingerbread Houses
10 a.m.-5 p.m. Thursday
Bakers, artists, families and businesses create Gingerbread houses that go on display for a monthlong competition at the Visitors Center.
An Inner West Street Association promotion, visitors to the display vote for their favorites, with winners announced at the Annapolis Chocolate Binge Festival on Dec. 7. First prize is $200.
Winners in several categories will remain on display through Dec. 19.
It’s sno time
7 p.m. Saturday
Warren Miller ski films are well known for daring shots, amazing locations and talented athletes.
“SNO-CIETY” is the latest entry from the company that continues the work of the late skier and filmmaker, highlighting the sense of community that bonds those who love hitting the slopes.
General Admission to the screening at Maryland Hall is $21, plus taxes and fees.
Blended sounds
7:30 p.m. Saturday
Paapa-Berchie merges hip-hop, contemporary R&B, Afrobeats and pop to create a vibrant sound.
He’ll be at the Live Arts Maryland studio theater at Annapolis Mall.
General admission is $30, with discounts for students, active duty military and seniors.
Holiday glow
5-9 p.m. Sunday
Every year, Sandy Point State Park lights up with holiday displays in a drive-through fundraiser for the SPCA of Anne Arundel County.
Lights on the Bay MD is open nightly through New Year’s Day for general admission, a 2-mile drive through 70 animated and stationary displays. Admission is $20 per car, plus taxes and fees.
A series of special nights starts at 5 p.m. on Friday and Saturday, when the park opens for pet owners for a walk through the lights. Admission is $20, plus taxes and fees.
Another light
4-5 p.m. Sunday
The Chesapeake Chapter of the United States Lighthouse Society will celebrate the 150th anniversary of the Thomas Point Shoal Lighthouse, one of the Chesapeake Bay’s most recognizable landmarks.
The evening includes a dramatic presentation on the Fresnel lens and how it transformed lighthouse illumination, as well as a commemorative lighting ceremony.
Attendance is limited to 150 guests. Admission is $22 plus taxes and fees.
Paca holiday
11 a.m. Monday
Historic Annapolis has decorated the William Paca House and Garden, home to one of the Maryland signers of the Declaration of Independence, for the holidays.
One-hour tours are offered Mondays, Fridays and Saturdays through Dec. 22. Admission is $15 plus taxes and fees.




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