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The Compass

Annapolis, by bike.

Annapolis rides best when you treat the weather as your ally and the map as a work in progress. The land is easy underfoot and the shoulder seasons are long and pleasant, which counts for a lot. The paths and lanes here are still few and scattered: a good climate and gentle ground are waiting for a network to catch up.

Rolling terrain 28.0 mi network 7 good-riding months ~0.4% ride to work
Last updated · 2026-07 See something off? Tell us →
Where it is
Annapolis — rolling terrain in Maryland
Heading here for school?

United States Naval Academy — the cycling guide for students & parents →

The shape

The shape, at a glance

The whole city in a screen: the profile, the ground and the riding year, and a few sourced figures.

The profile
ConnectedCalmAll-SeasonWelcomingRoom to RoamCar-Light

Strongest on All-Season. Welcoming is the near edge, with the most room to grow.

Ground & the riding year
Gentle
Mighty

The ground is gently rolling, so there are no real climbs to talk yourself out of. It stays easy enough that pace, not grade, decides your day.

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

The riding year. About 7 comfortable months, with a hot summer and a cold winter to ride around.

Comfortable Hot & humid Cool & short days
Spring and fall are long and comfortable, with only a hot stretch in the heart of summer to plan around. The winter months turn cool rather than harsh, so a rider willing to layer can keep going most of the year.
Terrain · Open-Meteo Elevation (Copernicus DEM) · 2026-07
Season · Open-Meteo (ERA5 climate reanalysis) · daylight by latitude · 2026-07
By the numbers
Bike network
28.0 mi
mapped cycleways and paths (OpenStreetMap)
Source · OpenStreetMap (Overpass): highway=cycleway/path
Everyday riding
~0.4%
of commuters bike to work (Census ACS)
Source · US Census ACS 5-year, table B08301
Is it a good month to ride? Read the year month by month.

Is it a good month to ride in Annapolis?

This is the shape of a usual year here — a climate pattern, not a forecast. Pick any month.

Month

January usually turns cool, with short days.

Lights and a warm layer, and it is yours. Cool months almost always ride better than they look from indoors.

February usually turns cool, with short days.

Lights and a warm layer, and it is yours. Cool months almost always ride better than they look from indoors.

March usually turns cool, with short days.

Lights and a warm layer, and it is yours. Cool months almost always ride better than they look from indoors.

April usually reads as comfortable.

Ordinary clothes, ordinary ride. In the long-run pattern this is one of the months that asks nothing special of you.

May usually reads as comfortable.

Ordinary clothes, ordinary ride. In the long-run pattern this is one of the months that asks nothing special of you.

June usually reads as comfortable.

Ordinary clothes, ordinary ride. In the long-run pattern this is one of the months that asks nothing special of you.

July usually runs hot and humid.

The heat shapes the hours, not the year: early mornings and evenings are the friendly windows. Carry water, take the shade, slow down a little.

August usually reads as comfortable.

Ordinary clothes, ordinary ride. In the long-run pattern this is one of the months that asks nothing special of you.

September usually reads as comfortable.

Ordinary clothes, ordinary ride. In the long-run pattern this is one of the months that asks nothing special of you.

October usually reads as comfortable.

Ordinary clothes, ordinary ride. In the long-run pattern this is one of the months that asks nothing special of you.

November usually reads as comfortable.

Ordinary clothes, ordinary ride. In the long-run pattern this is one of the months that asks nothing special of you.

December usually turns cool, with short days.

Lights and a warm layer, and it is yours. Cool months almost always ride better than they look from indoors.

The longest comfortable stretch runs August through November, and 7 of the twelve months read comfortable in all.

7 comfortable 1 hot & humid 4 cool & short-dayed
Source · Open-Meteo (ERA5 climate reanalysis) · daylight by latitude · 2026-07 · a long-run climate pattern, not a forecast
The six dimensions

Read it dimension by dimension

Tap a dimension to jump to it.
Connected Room to grow Growing
Does the network join up into usable routes?
The pieces that exist don't yet link into many through-routes, so getting across town by bike still means stitching things together yourself. That's the clear opportunity here: not more places to ride, but connections between the ones there are.
Source · OpenStreetMap (Overpass): highway=cycleway/path
Calm Room to grow Growing
How much riding is away from fast traffic?
Most riding still shares space with faster traffic, and the quiet, protected stretches are limited. It's a gap, and the kind that grows most as calm routes get added one at a time.
Source · OpenStreetMap (Overpass): highway=cycleway/path
All-Season Solid
How rideable is this place across weather and seasons?
This is the city's steadiest strength. The rideable window runs wide on both sides of summer, and the cool months stay workable, so the calendar rarely tells you no.
Source · Open-Meteo (ERA5 climate reanalysis)
Welcoming Room to grow Growing
How easy is it for a newcomer or nervous rider to get started?
The terrain won't scare off a beginner, which is a real head start. What's missing is a set of easy, low-stress starter routes, so a newcomer's first job is finding the calmer streets rather than tackling any hill.
Source · Open-Meteo Elevation (Copernicus DEM); OpenStreetMap (Overpass): highway=cycleway/path
Room to Roam Room to grow Growing
How far can you genuinely go by bike?
With a modest network, the distances by bike are still short, and longer outings lean on shared roads. The gentle ground means the ceiling will rise naturally as more miles connect.
Source · OpenStreetMap (Overpass): highway=cycleway/path; Open-Meteo Elevation (Copernicus DEM)
Car-Light Room to grow Growing
How well can the bike replace car trips here?
Only a small share of people bike to work here so far, so the bike is more a choice you make than a default the town is built around. That leaves plenty of everyday trips as an open invitation.
Source · US Census ACS 5-year, table B08301
Take action

Where Annapolis has the most room to grow

The two dimensions with the widest opening here — read as an invitation, not a verdict. Every one of these is something a resident can move, and none of it requires expertise or a fight.

WelcomingGrowing · most room to grow

Welcoming grows person by person. Nearly every place has more riders in it than the streets suggest — coalitions, community shops, ride clubs, school runs — and they are the invitation.

Find the people already riding here, then bring one more person along.

Nothing in this section is sponsored and nothing carries an affiliate link — that separation is the point. All of it, joyful half included →

Find your people

Real, active groups we checked by hand — coalitions, community shops, ride clubs, and programs worth an email. Each is verified and dated. If one has gone quiet since we looked, tell us and we'll pull it.

Statewide

  • Bike MarylandBike Maryland is a statewide nonprofit that promotes bicycling, works to improve riding conditions and safety, and provides a voice for bicyclists across Maryland.Verified · 2026-07

National

  • PeopleForBikesA national bike-advocacy nonprofit and industry coalition that works on better bike infrastructure and policy, and publishes the City Ratings that score how good U.S. cities are to ride.Verified · 2026-07
  • Rails to Trails ConservancyThe national nonprofit behind the rail-trail movement, turning former rail corridors into multiuse trails and running TrailLink, a free finder for trails near you.Verified · 2026-07
  • League of American BicyclistsA national bicycling advocacy and education nonprofit that runs the Bicycle Friendly America awards program, the Smart Cycling rider-education courses, and a nationwide network of local advocacy groups, clubs, and certified instructors.Verified · 2026-07
  • Adventure Cycling AssociationAdventure Cycling Association is a national nonprofit for bicycle travel, founded in 1973, that maps long-distance routes, helped build the U.S. Bicycle Route System, runs guided tours, and advocates for better cycling routes.Verified · 2026-07
  • Safe Routes PartnershipThe Safe Routes Partnership is a national nonprofit that helps make walking and biking to school and around the neighborhood safe and easy for kids and families, supporting local Safe Routes to School programs with resources and policy expertise.Verified · 2026-07
  • Move UnitedMove United is a national nonprofit whose local chapters offer adaptive sports and recreation, including adaptive cycling and handcycling, so people with disabilities can ride and stay active in their communities.Verified · 2026-07

Nothing here is sponsored, and no link is an affiliate link — that separation is the point.

Guides that help here

If the profile got you thinking

Short, practical guides: choosing a bike, riding with confidence, and the kit that helps.

City bike, hybrid, or e-bike? Pick the type that fits your trips. Read the guide → Getting started, with confidence From rusty to riding, at your own pace. Read the guide → How to choose an e-bike The biggest single spend, done right. Read the guide → Locks & theft prevention Lock it so it is still there later. Read the guide → Lights that get you seen The cheapest real safety upgrade. Read the guide → Carrying errands by bike Racks, baskets and bags for a car-light week. Read the guide →

Browse all guides →