Bike enthusiasts call this a “right hook,’’ explained David Watson, executive director of the advocacy group MassBike. So pugilistic are encounters with motorists that cyclists borrow terminology from boxing: a “left cross’’ is when a motorist turns left across the path of a biker going straight.

The hair-raising negotiation of Charles Circle was not the only fright. As the newbie pedaled tentatively through windblown rain down Beacon Street, a teal Chevy Cobalt , its driver clearly impatient with the cyclist’s pace, accelerated and blew past, then made a sharp right, forcing the rookie’s second screeching halt of the morning.

The former Olympic cyclist, who estimates she has ridden enough miles to travel to the moon, is convinced that Boston bikers can cycle with the cars, even in a city thrice named by Bicycling magazine one of the nation’s worst for bicyclists. To prove her point, one recent morning Freedman led an inexperienced cyclist on several typical bike-sharing routes, each less than 2 miles and 30 minutes long.

“Bike share will transform Boston into a world-class biking city,’’ she said. “All I see is this incredible upside.’’

Now the question becomes whether enough people will put their lives on the line riding on bicycles along city streets that even Mayor Thomas M. Menino, who has led the push to make Boston bike-friendly, describes as “old cow paths turned into roads.’’

Over the next few weeks, officials expect to name the company with which they would negotiate a contract on how to run the system. They hope the program will lead to tens of thousands of people saddling up in Boston daily.

If all goes as planned, Bostonians and visitors will ride these bikes to run errands, reach their workplaces, travel from tourist site to tourist site and from meeting to meeting. All of this, officials say, will make drivers and bikers more respectful of each other, and possibly take some cars off the city’s road ways.

This is biking in Boston, city of clogged streets, minimal bike lanes, and drivers who often act as though two-wheeled vehicles have no right to the road. City planners want to change all that - by putting more bikers in the streets. They intend to roll out what would be the nation’s first citywide bike-sharing system next spring, making hundreds of bicycles at dozens of stations across Boston available to anyone who can swipe a credit card.

A bicyclist on his first ride in Boston pedals tentatively into the furious rush-hour snarl of Charles Circle on a stormy morning. He signals that he needs to go left. The BMW behind him wants to go straight. Guess who wins. The biker brakes hard to avoid a collision, earning an angry honk from the Honda Civic behind him.

The bike ride was not all bad. Freedman’s routes - from City Hall Plaza to Kenmore Square, then to the South End, then to South Station, then back to City Hall - demonstrated the efficiency of biking instead of walking or taking public transportation. The city-owned bicycle was comfortable and stable. A biker’s-eye view of Boston is quite pleasant, when the biker is not terrified.

Appointed by Menino in 2007, Freedman is spearheading the effort to make Boston better for bikers; she has overseen such developments as citywide bicycling events, an annotated bike map, miles of new bike lanes and paths, and dozens of new bike racks. Bicycling magazine has changed its tune: In June 2008, it named Boston “a future best city’’ for biking.

Bike sharing is the next step. The city envisions making available between 1,000 and 3,000 bikes at stations 300 or 400 yards apart, located at subway and bus stops, main squares, tourist sites, and across city neighborhoods.

Riders would probably have the option of subscribing to the program for an annual fee, which would allow for discounts, or day passes. BikeNow, one of three companies the city is considering to run the program, would charge $2.50 for a day pass or $40 for an annual subscription. Each would allow cyclists unlimited rides of less than 30 minutes, but longer rides would be charged at an hourly rate, said Amy Trus, one of the Boston University School of Management graduates - class of 2009 - who formed the company. Cheap but functional helmets, Trus said, would be sold for $6 at nearby stores.

The bikes would have locks sharers could use during stops, but they would have very little value to thieves, said David Boyce, who runs the bike-sharing program for another company Boston is considering, Veloway.

A subsidiary of the France-based company Veolia Transportation, which operates the MBTA’s commuter rail system, Veloway would use bicycles that would be relatively heavy compared with bikes sold in shops, and their components would be hard to remove, Boyce said. He said the bike-sharing program Veloway runs in London has seen very little theft or vandalism of the bikes. (A third company Boston officials are considering is Public Bike System, which runs BIXI, Montreal’s bike-sharing program.)

Freedman said bike sharing in Boston would be as popular as it has become in Paris, where the city had to double its fleet of 10,000 bikes and 750 stations several weeks after its program opened in 2007. Today, on average, the 20,000 shared bikes in Paris are ridden some 200,000 times.

Watson says Boston is lagging behind in cycle-friendly infrastructure. The city added five miles of bike lanes last year and is planning five more for this year, while New York has added 200 miles in the past three years. Watson believes a bike-sharing program will force Boston to become bike-friendlier faster.

Safety is a bigger problem. The new bicycle law in Massachusetts addresses some dangers - for example, “dooring,’’ when a car occupant opens a door and hits a biker, is now a ticketable offense. Supporters cite studies that suggest biker fatalities and injuries decrease the more cyclists are on the road.

“As people see more cyclists in the streets of our city they’ll be more aware of the issues of safety,’’ Menino said in an interview. “It works in other places, it will work in Boston.’’

Menino, who has become an avid biker, is planning campaigns to educate drivers on how to coexist with bikers. But cyclists are also part of the problem: They ride on sidewalks, run red lights, and stop in right turn-only lanes, all of which infuriate drivers. Freedman pointed out a couple of riders who rode, helmetless, the wrong way on East Berkeley Street in the South End. With more bikes on the street, the city will have to “make sure bikers bike safely,’’ Freedman said.

Nearby, Rich Coombs, whose family owns Community Bicycle, a bike sales and service shop in the South End, expressed doubt that bike sharing would work in Boston.

“There are tight roads to begin with - roads dating back hundreds of years, little cow paths,’’ he said. “There’s barely enough room to squeeze by with narrow handlebars.’’

Still, those little cow paths give Freedman hope.

“People could live here before there were cars,’’ she said, “and they can do it again.’’

David Filipov can be reached at filipov@globe.com.

© Copyright 2009 Globe Newspaper Company.