Go west or north of the city. Anywhere pretty much will have plenty of hills.

We got hella river valleys around here! I grew up around Ellicott City and there are some mean hills down around Old EC (check out River Rd/Ilchester Rd/College Ave). That area ties into some two-lane country roads extending out into western Howard County (Triadelphia area) that my distance cycling buddies train on. You can kind of noodle around in and out of the Patapsco River valley to put on elevation. There are similar situations around rivers/reservoirs like Prettyboy or Loch Raven. All of this is about a half-hour drive outside the city.

Nice long uphill from Charles on the Jones falls to the top of Druid hill park - has a switch back up to the park entrance then up from there. You can continue on the trail by the zoo - take a little down hill on another switch back - then cut across the service road that goes behind the zoo - a couple of good hills back there- it makes a loop and reconnects to the trail by the pool at Druid Hill.

Back hills of Druid Hill Park. Loop from behind forestry through the hills towards Woodberry. Take the switchbacks up, head through the disc golf course, and then through the park back towards the safety city, and repeat.

It’s called mountain pass trail, I just accidentally discovered it, very hilly

It’s hilly and pretty and relaxing but not that difficult. If you want challenging hills, then do the Jones Falls Trail from the Woodberry Apartment on Coldspring Lane back towards Cylburn Arboretum. It’s a constant uphill trail for quite awhile.
It’s also a trail and nice but more along the road compared to the less hilly path that’s besides the trees behind the zoo.

Up and down the pagoda hill in Patterson park.

Druid Hill Park has some great elevation change and drivers aren’t as much of a PITA as they are in the rest of the city if you’re trying to do some road riding. Always best to bike to where you’re trying to train (get some extra work in and you don’t have to drive anywhere!)

Hunt Valley. 83N out of the city to Shawan road exit west, then take an immediate right onto Western Run Road and park in the park and ride lot there on your right. There will be other cyclists parking there. Take western run road away from Shawan and there are TONS of hills. You’ll see lots of cyclists out there Sat and Sun mornings. If that lot is full you can drive a little further west on Shawan until Oregon ridge Park. Park there and ride north on Cuba Road. Use the Strava heat map to find the most traveled roads by cyclists. Prior to having kids I used to do a lot of long rides up there when I was training for long triathlons. If you want something closer to the city, try the loch raven reservoir/Long Green/Baldwin area. There are some decent hills but more vehicle traffic. Hunt valley is really where you want to ride and is worth the drive. Plus, you can refuel at Wegmans after your rides in HV.

Mt Washington has fantastic climbs (for the area). Just start riding around and hit every road. Crossing Falls Road to Lake and Bellemore is good too.

To answer your question: Druid Hill Park is hilly but it's only 1.5-2 miles of moderately steep rollers, my recommendation for in the city limits is Lake Ave, Bellemore Rd and Poplar Hill road which are 3 the northern most roads that run between Falls rd and Roland Ave. They're all right next to each other and the whole stretch between Falls and Roland is winding hills.

My true recommendation is don't ride in the city. Baltimore has some of the worst drivers in the country IMO (note the number of white bicycles ling the city streets). Right outside of the city you have tons of great riding options.

Feel free to DM for info on cycling groups and routes in the area.

The key to cycling in Baltimore is getting to Hillside rd

Patapsco state park. Lots of trails to ride on.

Start at the harbor, and ride north. It's all uphill. I used to ride from Fell's Point to the Loch Raven Reservoir and back a couple of times a week.

My recommendation is don’t listen to this person! So many people bike everyday in the city - for recreation and to actually get around. There’s great riding of all styles - playing in traffic downtown, coasting in and around parks, rolling through the more suburban-y parts within city limits. The more bike riders on the streets the better it is for everyone…

OP isn't talking about commuting. They're training for an actual race, so stopping at lights and signs doesn't fit with that. It becomes either them getting bad training for their race or disobeying traffic signals endangering themself and others. If you're talking about commuting, sure, it's fine, but that's not the case here.

This one will kick your ass. Also Mt. Washington has some areas with 19% grade.

Patterson park is the answer. There's a reason why they have competitive bike races there.

Near / In Patapsco Park. A favorite is the loop of Ilchester Rd -> Beechwood Rd -> Bonnie Branch Rd.

Another is to go up and down Gun Rd.

Loch Raven reservoir and surrounding area. Providence Rd, inside the Hampton community. Dulaney Valley Rd. Endless rolling or steep options out there and fairly biker friendly

Echoing a few other comments:

Starting from the Inner Harbor area, Maryland Ave has a dedicated bike lane that runs through the city. Lots of stop lights but it is relatively hilly so it's a good warm up for once you get out of downtown. Swing on to Falls road right next to Baltimore Bike Works then ride up through Hampden following the signs for Roland Park (this route also brings you past Lake Ave and adjacent roads which have some absolute beasts of hills so when you get to Lake Ave definitely poke around). Loop Roland Park for some good hills and lake views then get back on Falls Road and head towards Joe's Bike Shop in Mt. Washington (to add as much distance as you want head the opposite direction up Falls Road then double back). Cross the bridge across from Joe's and link onto Jones Falls Trail. Follow the trail until you hit Druid Hill and take a left upon entering. This brings you to the big hills others have mentioned, ride up and down to hearts content. When tired, exit Druid Hill by the swimming pool, take the pedestrian path back down to Falls Road, back down Maryland Ave, and you're in the Inner Harbor. If you just do the loop without and extras it comes out to ~20 miles. It's the best mix I've found of bike paths, dedicated bike lanes, and safer roads. There is also good elevation along this route, and you can double back on any hills you like or ride it in reverse to hit hills from the other direction.

If you get tired of battling cars and want to opt for a safer, flatter option, the BWI loop connects pretty directly to the Baltimore - Annapolis bike path so that is an easy way to crank out some miles without worrying as much about stoplights. Not a ton of good elevation, but not totally flat either.

Also, as long as you are hyper-aware and seek out bike lanes downtown I've found Baltimore to be an unexpectedly rideable city :)

I believe Lake Avenue was part of Bikes & Beers last year and as we approached it another rider turned to me and said “get ready for the worst hill in Baltimore”. 🙂

"Playing in traffic downtown", is there really a cyclist who wants this?? Urban biking IMO is the worst! The fumes alone, plus the noise, and of course all the hazards hatching your vibe. Dirt track is the best but a country road in farm country or woods is still superb.

BaltCo needs better shoulders though, so many 2 lane roads like Greenspring Ave or Tufts are so pretty to ride otherwise.

We moved to NE Baltimore and I bought an ebike specifically to deal with some of the hills up this way

Where is the best place to park and ride this loop? Thanks!

As someone who grew up north of hunt valley I agree with this, there are lots of beautiful roads to ride on up that way. However I’d stress that many of these backroads do not have shoulders much less bike lanes or have blind curves so please please be careful, especially on more of the main roads with traffic but no shoulder. I realize that cars are supposed to yield to bikers but I’ve seen too many near misses growing up. So please use caution, and yes this is equally applicable to the bikers and car drivers out there.

You can park in Woodberry and immediately hit a hill in either direction, or anywhere around the reservoir/safety city/baseball fields. The disc golf area I would recommend against as parking is tight as is.

Could go up to Ruxton and Greenspring Valley and do a stop at John Brown Coffee or Velocinno, head back on Falls Rd and take Bellemore up to Roland. Easily get 2 to 3k climbing there. Baltimore Bicycle Works does a route similar to this Thursday night during spring and summer.