The first ever Pittsburgh to Cumberland, Md COMBO Ride!
What the hell is a Combo Ride? Well, after years of hearing so many cyclists claim that they would like to do a ride from Pittsburgh to Cumberland, Md, BUT....do NOT want to do the same old same old of three days along the GAP Trail ONLY!
And we AGREE! Yes, the GAP is a wonderful experience, but it does get really repetitive.
So, we are introducing the first ever Pittsburgh to Cumberland Combo ride where we do BOTH one and a half days on the GAP, and one and a half days along some of the most beautiful & scenic roads in Western Pa and Md. AND....as ALWAYS, the road sections have been thoroughly vetted by the Ride Genius Team, ensuring low volume roads with paved surfaces. Please NOTE that the road sections do have climbs and are NOT for any riders who disdain hills!
Dates for this 3-day ride will be this Fall (sometime between Sept 13th and Sept 24th & will be finalized by May 25th).
Ride fees will include full SAG, hotel stays, transportation*, luggage service daily, rest stops, Ride With GPS routes, and daily après-ride Happy Hours!
For more Info: Call Phil Heffler 301-693-4503, email Phil at <pheffler@aol.com>, or use the website contact form.
Equipment: We suggest bringing a bike that is suited for road and trail, such as something with tires at least 28mm wide (but 32 is better).
* Starting points & transportation is tricky, due to the fact that we will have two different starting points.
Option 1: For those that are from the Pittsburgh area. They will start the ride in Boston, Pa on day 1. Then, after day 3's ride into Cumberland, Md we will transport you, your luggage, and bicycle back to Pittsburgh. Expected ride fees to be $949 double occupancy & $1,249 single.
Option 2: For those that are from the DC, Baltimore & Mid-Atlantic. These riders & gear will be picked up a day earlier in Cumberland, Md, and then transported to Pittsburgh for the next day's ride start. Because of the extra costs of truck rentals, overnight hotel stays, etc. in Pittsburgh, add $150 to the ride costs, So $1199 double occupancy & $1399 single.
Category: tours
Bike tours of three days or more, typically a full week (5 or 6 days of riding). Roads are typically marked; cue sheets and GPS files provided. Dine at restaurants and overnight in hotels or B & Bs.
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2026 GAP/Road Combo Ride (Fall 2026)
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Pedal Pittsburgh to Frederick 2026
The 2026 Pedal Pittsburgh to Frederick (MD, a.k.a. PP2F) is totally supported with daily SAG support, luggage transport, rest stops, hotel reservations, post-ride happy hours, marked courses (bright white arrows), GPS and two SAG vehicles following close by for the 305 miles, over 5 days.
NOTE: For those riders from the Pittsburgh area, we start Monday Morning at 7:30am from Downtown Pitt at the Joinery Hotel. For those that are from the Mid Atlantic, we van you to Pittsburgh on Sunday morning, July 12th, from Frederick, MD.
Here is each day’s mileage, stays, etc.:
• Day 0 (Sunday, July12): Van transportation for bikes and luggage from Frederick MD to Pittsburgh, PA for those who live near Frederick.
• Day 1 (Monday, July 13): We leave from downtown Pittsburgh and take the GAP trail to McKeesport (all paved). Then we pick up the roads from there all the way to Ohiopyle Pa. 72 miles, with rolling hills and one big climb into our overnight. Ohiopyle has some neat restaurants (as do every night’s stays).
• Day 2 (Tuesday, July 14): Ohiopyle to Deep Creek, MD. 61 miles. We go over Mt. Davis (PA's highest point) early this day, before about 15 miles of terrific down hills along perfectly smooth & low traffic roads to Grantsville, MD and lunch, Then it's 25 miles to Deep Creek & our stay on the lake at the 5-star Lake Front Lodge. There is a grass beach there so bring swimming gear.
• Day 3 (Wednesday, July 15): Voted the most scenic & beautiful ride of the week! Deep Creek to Rocky Gap Resort (Near Cumberland MD). 65 miles with the majority downhill as we start at 2400 ft above sea level and wind up 25 miles later in Westernport MD at 500 ft above. Most of it is along the Savage River, which is incredible! Then, after a long but easy 14-mile climb (3% grade) to Frostburg MD, we finish with another 14-mile downhill to Cumberland and then on to Rocky Gap (If you are a golfer, bring your clubs along; some are playing the championship course that day....3:30 pm tee off time). Or just take in a swim or maybe some Blackjack at the Casino!
• Day 4 (Thursday, July 16): 52 miles over five mountains – Martin’s, Polish, Green, Town Hill, & Sideling all the way to Hancock MD for lunch, then 18 miles to our overnight at Clear Spring MD and a quaint dinner at an Italian Restaurant. A FAVORITE Day for hill climbers (5400 feet of climbs with great views and long, safe descents).
• Day 5 (Friday, July 17): Clear Spring to Frederick, MD. 63 miles along some truly picturesque Civil War battlefields and historic sites (Antietam, Harpers Ferry WV, site of the John Brown's attempt to take over the Union's armory.) Literally a masterpiece of Civil War sites! After Harpers Ferry, we lunch at Brunswick MD before our final climb over the Catoctin Mts and down into Frederick MD (The MECCA of Road Cycling with even more historic sites with great restaurants).
• Then, after a one-night stay in Frederick, we van you, your luggage, and your bike back to Pittsburgh on Saturday morning (July 18). ETA back in Pitt at 12:30pm.
Costs are $1300 for Double Occupancy & $1750 for Single Occupancy. We currently have a few spots open. 11 signed up so far; this is a small tour – we can handle 16 (five more people).
For more info call Phil Heffler at 301-693-4503 or use the website contact form.
Also:
--- We will be hosting a 3-day Pitt to Cumberland MD COMBO ride (both the roads & GAP Trail) that will be between September 13th - September 24th. Exact dates to be decided soon. Costs for all @ $950 double occupancy and $1250 single.
--- A 3-day ride at the PA Grand Canyon Pine Creek Rail-Trail with two days seeing the Little League World Series in Williamsport PA. August 2026. No fees for this one, just make your own hotel reservations. -
Deep Creek MD – October 4 2025
I am looking at doing a one-day ride Saturday, October 4th, at Deep Creek, MD.
We would stay at & ride* from the Lake Front Lodge at 10:30am, do a 43-miler down the Savage River along the PP2MD Spring Lick Rd route that we did in July, and then reverse up the river and climb Dry Run Rd (this would be a different climb from the downhill). Dry Run is a Cat 3 climb...tough but doable...total climbing is 3600 ft.
*Timing Tip: From Frederick or Pittsburgh, Deep Creek is a 2-hour drive, so plan on leaving by 7am to give enough time to get ready Saturday morning before the ride starts (10:30am).
We would stay overnight at the Lake Front Lodge, which has lake-adjacent rooms @ $230 a night. Water should still be warm so bring your swim trunks!
We are calling this ride the OFFICIAL REX BALLINGER RETIREMENT RIDE...Who is finally throwing in the Towel!
In lieu of a gold watch, just buy him a walking cane, prune juice or a membership to AARP!
For those that have never ridden this course, it is a 5-star ride, and got RAVE reviews from ALL who did it on Pedal Pitt 2 Md in July.
$30 ride fee includes cue sheets, GPS routes, & après ride snacks/beers/sodas.
Please let me know by August 15th so I can make the needed reservations.
Note: Some rooms have two beds, some king-only, so if you want to share a room, act quickly, as they will fill up.
OR...For those who just want to ride & do not want to stay overnight, you can use one of my rooms to shower, etc. before heading back home.
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Icebreaker Open
We are planning on doing our Annual Ice-Breaker Open bike ride here in da Burgh, Saturday, January 4th, 2025.
Bring in the New Year with a Hills & Thrills (Pittsburgh Style), and ride around beautiful North Park. Ride starts at 12:30pm (To let it warm up a bit). PLUS it gives Merry-Land riders plenty of time to get there that morning.
* 15-, 25- and 30-mile ride options (Plus, it NEVER SNOWS on a Fil Heffler Event)
Then, we will pick a great restaurant for dinner that night.
Out of towners, let me know, and I will assist on getting Overnight hotel reservations for you.
Interested? Contact us in the usual way.
Fil....Start your cycling year off right! -
Pedal Pittsburgh to Frederick 2025
The 2025 Pedal Pittsburgh 2 Maryland bicycle ride will be July 13th thru the 19th in 2025. Five days of riding, with over 310 miles of beautiful, low volume roads. Some optional bits on the GAP trail. Transportation back, Full SAG and Hotel overnights included. Contact us via this website.
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Jim Thorpe/Wellsboro
-Jim Thorpe Ride (Road & Lehigh Valley Trail)
* Tuesday, Sept 24th & 25th, Jim Thorpe Inn (overnight)
** 9-24 Tuesday: 1pm start. Cycle the Lehigh Valley Trail. Choose your distance....20-30-40-???
Dinner in town that evening
** 9-25 Wednesday: 8am start. 25 mile road ride up & over the mountain. Gorgeous views, with a 4-mile return to Jim Thorpe on the Lehigh Trail
Then we are off to Wellsboro PA and the PA Grand Canyon (by car). Arrive Wellsboro approximately @ 2pm.
Check into the Grand Canyon Motel (other motels are available). Explore the quaint town, dinner, drinks etc.
** 9-26 Thursday: 9am ride along the Pine Creek trail - one of the best in the state. Choose your distance....20-30-40-???
Then we head home that afternoon. All riders make their own hotel reservations.
Cost of the ride is FREE. But please contact Phil at pheffler@aol.com for the necessary details.
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Been on a Ride Genius Tour? How was it?
Hi folks. We want to place some testimonials and stuff on the website. We’ve added a couple, but a few more would be nice. We know you had fun with us, so put it in writing and Phil will buy your lunch on a ride (kidding – he never said that). Just reply to this post…and thanks.
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Pittsburgh to Frederick 2024
A 5 Day ROAD Ride from Pittsburgh to Historic Frederick, MD (The Mecca of road riding!)
Sunday, July 7th Thru Friday the 12th, 2024 * See Below
- 2 options:
1-For those that live in the Mid-Atlantic. We meet Sunday morning (July 7th) in Frederick at 8:30am. Then we load your bike and luggage on our truck, and we van you up to the 5-Star Sheraton Station Square Hotel in downtown Pittsburgh. Beautiful city with lots of sight-seeing and an optional ride through Pittsburgh that afternoon. Then we leave Pitt the following morning (July 8th) by bicycle.
2-For those that live in Pittsburgh area. We meet at the Sheraton for a Meet & Greet Happy Hour at the Sheraton Hotel at 5pm. Then, all cyclists leave Monday Morning (July 8th at 7:30am) for Day One. Upon finishing the tour on Friday in Frederick, we stay overnight in beautiful downtown Frederick. Then we van you and your bike back to Pittsburgh Saturday morning the 13th.
5 Days of riding over 300 miles of scenic, low volume roads with full support, luggage transport, SAG, rest stops every 20-25 miles, & hotel, motel & B&B’s included….and après ride happy hours daily.
And OH! Did I mention? The courses are boldly marked with directional arrows as well as GPS & route sheets to guide you along each day with 2 SAG vehicles always within a few miles from the riders.
Here are the daily destinations with approximate mileage **
Day 1. Pitt to Ohiopyle, PA. 72 scenic miles along PA’s Rust Belt. We stay adjacent to the Mighty Youghiogheny River. Bring your swimming gear, the Yough is great for cooling off after a long ride! 5600 feet of climbing.
Day 2. Ohiopyle to Deep Creek, MD. 60 miles with a climb up & over PA’s tallest point, Mt Davis. We stay at the Lake Front Hotel (Deep Creek’s best) with a grass beach from your room to the lake. 5000 feet of climbs.
Day 3. Deep Creek to Cumberland MD. 64 miles over the prettiest and greatest ride ever! Photo ops galore. 5500 feet of climbs. We stay in historic downtown Cumberland at the Fairfield Hotel.
Day 4. Cumberland to Clear Spring, MD. 5 mountain climbs today. We stay at the Holiday Inn Express in quaint Clear Spring MD. 54 miles with 5500 feet of climbs.
Day 5. Clear Spring to Frederick, MD. 58 miles with 3000 feet of climbs. For those from the Mid-Atlantic, the ride is over. For those from the Pittsburgh area, we stay overnight in historic, Civil War Frederick. Great restaurants, bars and sight-seeing. Then we van you back to Pittsburgh Saturday, July 13th.
Double occupancy cost is $1499. Single occ $1750. A $350 non-refundable deposit holds your spot. Balance due June 7, 2024.
For more Info: Call Phil Heffler at 301-693-4503 or email at Pheffler@Aol.com
** Pedal Frederick is not an easy ride. Cyclists should train well prior to the event to ensure maximum enjoyment during the week.

