I'm a planner. I started riding last year and on my first 25 mile ride, an organized club-type ride, I bonked. I also go through a ton of water so I make sure that I hydrate before and during a ride and plan water stops accordingly. I spend most of my planning to keep the engine fueled and operating properly. Routes are planned around the engine.

I plan most of my rides and most of the rides our club does. I'm the route planner guy around here. But sometimes I like to explore new areas. I'll lay out a general plan, but if I don't like the roads, I'll make detours. If the detours don't take me where I wanted to go, I'll use Google Maps on my phone to figure out an escape plan. When I'm riding alone from home, I'll often make it up as I go, but I already know all the roads around here, so it's not really exploring, just recombining known options.

I plan meticulously. As we don't have decades of riding behind us, I know pretty much what the physical limits are for the 3 of us who ride together, and how much driving to trailheads we can do in one day. We only ride the trails, but I've added mapmyride to my "tool kit" because it's so good at showing elevation changes. My goal is to put tread marks on every decent trail in my state, and at least one or two other states every year. Last year it was the GAP in Pennsylvania, not sure where it will be yet for this year. Fortunately for us there's a section of the Ohio to Erie trail right outside our door we use for fitness rides.

I've been riding my road bike in the same area for over 35 years so getting lost would be tough to do. On the other hand I just went out on a mountain bike ride for the first time in over 15 years, and I had to question a couple times where I might be. I did like the adventure part of it and will be adding a mountain bike ride into my weekly ride schedule.

If you do a route you use for training and know by heart, isn't that planned?

I always plan. I like to ride briskly and push myself and find ambiguity of route slows me down. I probably should do more less strenuous exploratory riding.

My usual rides are on one of 4 loops that are right at 30 miles each. However a whim will take me off the usual route if something catches my eye.

(that's why) You don't plan much: 'cause you live in a rural area. But come to the city, then one must plan -- so to find the better. When I further read your comment, I read your profile: Florida.
(misc note)
Where I live, cars that bring me trouble -- Excessively Close Side Contact. They are typically from 2 states: 1 of the 2 states being of Florida 'plates. The other being Texas)

That wouldn't be enough for me - I need more variety. Both in variations in distances but also routes and scenery.

Today I was ready for a 40 mile ride and though there are several 40 mile loops I can do from my driveway, there just wasn't anything that suited my mood. So I drove to a western suburb where I knew I could park near a good bike route and then rode further west. The first 10 miles was a familiar route, but then I rode past my mental map to new territory. I ended up in a nature preserve that has paved bike trails (an accident, I didn't know it was there) and turned east in the general direction of the car after 20 miles. Adventure!

Other than when I'm riding between states and have a definite date that I need to arrive, I rarely plan my rides. Sometimes I'll let the wind tell me which way to go (it is possible to do a loop with all tail winds, if you have the right geography). Sometimes I just head out and explore some road that I've never ridden on before.

Oddly, the last time I troubled myself to plan a ride was last year. My wife and I were riding in our favorite area (known as the O&C lands) and we actually plotted out a ride on ridewithgps and brought a tablet with us that has a gps. We dutifully followed the gravel road that was indicated right to where it ceased to exist. After a nice chuckle, we rode back up to the ridge and explored a different logging road that took us to a familiar road. That ride has since become a favorite of ours that we nicknamed Sugar because it involves riding on the C-line and turning onto the H-line (C&H Sugar).

I mostly do club rides so I just show up and follow the group.If I do plan a ride it's usually a last minute thing, I just grab enough food and figure out where to get water. When I get out there I decide when to turn back depending on how I feel.

Looigi I,
I should have said I plan all of my rides by making a map that I can access on my smart phone or my Garmin. I may ride a training ride without the map but it gets down loaded to Strave, mapmyride and Ridewithgps. They download
automatically from Garmin Express. And it transfers my activity to Myfitnesspal and the health program on my IPhone.

This is a nonsequitur if I ever saw one.

It doesn't matter whether I plan or not, because you'll still need to plan either way.

For me, planning is a matter of circumstances. On local rides I generally have a sense of what I want to do, and don't care if I get lost -- or to put it nicely, go exploring. It's all riding so it doesn't really matter where I do it, or even if I know. OTOH on longer rides with a specific destination, and riding range or time to consider, I do some basic route planning and at a minimum, have some sense of where I'm going, how I'm getting there, and how long it's take.

When doing multi-day touring, I'll roughly plan day to day, but I carry a map (you know, folded paper) and feel free to take detours if something interesting happens along the way.

To tho OP, you're starting in the Bronx and there are a number of good routes that take you out to City Island or up to lower Westchester. If coming to Westchester you can roughly parallel one of the 3 Metro North lines, and if you get lost or tired, work your way to the nearest station and Rail back to the nearest stop to your home. That opens up more nicer riding, and should relieve worries about getting lost.

Metro North is very liberal about taking bikes on off peak trains, but you'll need to go to Grand Central Station and buy the blue permit (lifetime, and cheap) because some conductors will ask for it.

BTW- I've ridden as far as Montreal, Philadelphia, and Rochester, riding no map, and just kind of winging it and keeping to a general direction.

Well I'm not getting lost in my own neighborhood the point was my range has gotten large enough to get out of my comfort zone, plus there is using my car to get me to different starting points.
This is what I'm talking about, I can't be in Rochester and be like "I ride in a general direction" for me that mean I'll wind up on the wrong side of one the finger lakes and have to do an extra 50 miles. To get back to your starting point or planned end point eventually you need to refine it more then "I ride in a general direction"

Don't forget Manhattan too, yes I have the trailheads to 3 major trails all within a 1.5 mile ride. Use them all the time

I ride mostly in the woods, many rides are pretty remote but I cannot Imagine how I could get lost,,I always have my Smart phone and It's GPS and,,google Earth...
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.Plus I can look up and see the sun or stars, I know how the planets move,,,

Getting lost In this day and age ? Really ?

Like jon c. I live in a rural area and know it pretty well. Tough to get lost. My planning consists of choosing an approximate mileage and heading out the door. Routes can always be changed on the fly if the mood strikes and the body argues not. If I'm looking for something new, meaning tossing the bike in the car and driving, I can usually find routes of various lengths online in an area I'm interested in riding.

I usually use Google Maps with the bicycling feature turned on, to explore new routes so that I know where I'm going when I try them, but when it comes to planning a ride, I usually just go out and pick a route from my grab-bag of favorites on the fly. I guess you could call this pre-planned randomness...

26th post is a planner , takes all sorts..

I didn't even plan my Multi month long tours much . bought a new paper map when I ran off the edge of the last one

Even In touring Other Countries. started in Dublin, departed from Aberdeen . got a visa extension at @ 6 months.

I didn't forget Manhattan, I just don't consider it quality biking, and all my riding there is based on getting to destinations and back.

Anyway, how I or anyone else plans or navigates rides is irrelevant to your situation. You mention your lack of sense of direction, so you need to do what's necessary to your needs. Options include carrying paper maps, or a cell phone with GPS and navigation.

Another method is that used by children and animals as they learn their world. Develop a network of known arteries venturing out from home, and push beyond known roads in small increments adding to the network. This gives you a network of familiar territory which becomes a larger target to shoot for when lost. Now if you get side tracked you can use your limited sense of direction to head back toward home until you cross one of the routes you know, and then can turn onto it and head for home.

This sense can be as wide or narrow as necessary. For example when I ride in Westchester, I have a few reference landmarks or boundaries such as the Hudson River and Long Island Sound, plus the various parkways, and maybe a few arterial road. So the county is divided into long narrow slices, and all I need to remember is what I'm between, ie. between the Bronx River and Hutchinson Parkway. Now if I'm lost, I can turn to either side, and when I hit a parkway, I know which way is toward home, and can parallel that until I hit roads I know.

If I'm going out to somewhere new or somewhere I'm not too familiar with, I'll do some planning but don't mind getting lost. I have the smartphone that works for me. If in familiar territory, I play it by ear.

Google maps bicycle mode and print out a couple of screen shots. Same for street mode. Also carry a hard copy of the local bicycle map. Guess I'm still old fashioned.

My bike route is planned in general. Go out this way, come back that way. Then I go to google earth and study the areas for places of interest and alternate routes. Maybe mark them down on my maps. Look at the weather just before I leave.

I live on an island and it's impossible to get lost, at least on the roads (not so hiking in the mountains). I pretty much do the same routes every week, because they work the best. I might on occasion randomly ride up neighborhood streets, but that's more killing time than getting in a workout. Or riding into / through downtown wastes too much time at stop lights.

scott s.
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I suspect that most riders have pretty much the same routes year after year, unless they go out of town or do an organized ride like a century ride.

How many?? Maybe a dozen and then its just a variation of that same dozen. Then once you've done those rides 10 times each, there's very little "planning" because you end up knowing them very well.

consider geography and climate when deciding where to go. I live in a very bicycle friendly city that is challenged climate wise (Midwest) in terms of winds and also a minor but pervasive north-south slope across the whole state. We live in the middle of the slope. So, I usually look at the weather before I leave and take wind direction into consideration. No point having to pedal uphill AND against the wind on the way back.

I usually don't plan rides. I'll check the weather forecast, but that's about it.

You are probably going to laugh, but I have an old Garmin eTrex Legend (the old blue one) handheld GPS (but with the bicycle handlebar mount), clipped onto my handlebars. Turn it on and go. I've been in the west end of Richmond, VA since 1996 and know all the streets, side streets, shortcuts, etc... so it's darn near impossible to get lost.

My bike takes me places, it's really nice that way. Sometimes it follows other people, maybe they plan, I don't know, never ask.

Marc