4 cycling, mountain biking, running, and other events in Portland, Connecticut
From big races to Saturday morning group runs—find cycling, mountain biking, running, and walking events and connect with the local endurance sports community.
Portland
4 events in Portland-
Sat, Jun 20, 2026 at 11:59 PMSee full details
Lions Roar – Cycling for our Community
Presented by: Portland Lions Club
Lions meet the needs of local communities and the world every day because they share a core belief - to serve their community.
Lions have a dynamic history. Founded in 1917, we are best known for fighting blindness, but we also volunteer for many different kinds of community projects - including caring for the environment, feeding the hungry and aiding seniors and the disabled.
100% of the proceeds raised from this event will be used for charitable causes.
For more about Lions Clubs, go to www.lionsclubs.org
Rain or Shine Event - Sorry No Refunds
Bike Helmets Required for all riders
E-bikes welcome on all routes
Same day registration available (fee goes up $5.00 for each ride) but we cannot guarantee a tee shirt will be available
Riders under the age of 18 must have a parent or guardian sign consent form
Must register by May 1 in order to guarantee that you will receive a t-shirt
Registration from 8am – 10am at Riverfront Park
Registration for Gravel Rides only at Bransfield Park from 9-10am
Some historic sites along the rides will include the Portland Reservoir and Meshomasic Forest. In the late 19th century and again in the 1940s two quarries in the Meshomasic State Forest were quarried for feldspar and mica. The quarries are still open to the public and rock collectors to explore. From the early 1950s to 1970s Nike Missile Site HA-36 was located off of North Mulford Road in the Meshomasic State Forest. It was one of over 300 missile-defense sites around major cities during the Cold War. Nike Ajax anti-aircraft missiles were located at HA-36 to protect Hartford's aircraft industry from Soviet bombers. There are eight miles of dirt roads, originally built by the CCC, open for seasonal driving in the forest. Hunting, mountain biking, off roading, and hiking are some other activities available in the forest.
Other sites along the road rides include the Arrigoni Bridge which connects Middletown and Portland and Brownstone Adventure Sports Park on the right, which used to supply quality brownstone from New York and Boston to San Francisco, and employed over 1,500 people during the 1850's. More than 25 ships transported the stone to major population centers in the United States, Canada and even England. The brownstone quarries in Portland, Connecticut, owe their existence to millions of years of prehistoric sediments accumulating in the Connecticut River. Quarried as far back as the 17th century, the brownstone around Portland proved soft enough to allow for carving and polishing, making it one of the most desirable materials for gravestone markers and building construction for nearly three centuries. Portland’s location along the Connecticut River allowed for easy transport throughout the state and, later, the world.
Route Choices (see descriptions)
Road Rides - 63 mile or 42 mile
All road Rides leave from Riverfront Park, 284 Brownstone Ave, Portland CT
Gravel Rides – 35 or 41 miles
All gravel rides leave from Bransfield Park, 160 Rose Hill Rd, Portland CT
Road Ride – Metric Century (63.7 miles) (includes tee shirt, food stops (2) and after ride meal)
Route will start at Riverfront Park in Portland and meander through Portland, Glastonbury, Manchester and Hebron with some of the ride on the Charter Oak Greenway. Recommended start time between 8-9am depending on speed, slower riders should plan to start at the earlier time
https://ridewithgps.com/routes/45437707
Road Ride – 42 miles (includes tee shirt, one food stops and after ride meal
The beginning of this ride will be the same as the metric splitting off around 17 mile mark. Recommended start times 9-10am depending on speed, slower riders should plan to start at the earlier time
https://ridewithgps.com/routes/45437935
Gravel Rides
Gravel Ride – Basic (35 miles) includes 1 water / food stop and hot lunch at end of ride
Will be on dirt roads in the Meshomasic Forest and the Airline Trail as well as paved roads, be sure to have a bike computer or the printed out cuesheet (available on day of ride) for this ride as there are not many road markers in the Mesh. Recommended start time 9-10am, slower riders should plan to start at the earlier time
https://ridewithgps.com/routes/45543674
Gravel Ride – Spicy (41 miles) includes 1 water / food stop and hot lunch at end of ride
Same as basic ride but incorporates trails and single track which does have rocks and roots. There will also be a beaver dam crossing across a wooden footbridge which requires walking across with your bike then stepping on some rocks to cross. Recommended start time 9am
https://ridewithgps.com/routes/46160101
GRAVEL RIDES ONLY DEPART FROM Bransfield Park, 160 Rose Hill Road, Portland, CT
Registration Cost:
63 Mile Road or Gravel Rides (includes lunch, t-shirt and 3 food / water stops) $55
41 Mile Road Ride (includes lunch, t-shirt and 2 food / water stops) $55
35 and 41 Mile Gravel Rides (include lunch, t-shirt,1 food / water stop and restroom / water stop at Airline Cycles) $55
T-Shirts provided at no additional charge when you register for one of the rides. If you want an extra shirt below are prices:
T-Shirts: $17 Small to XL as well as child sizes / $22 XXL-5XL
Hot Lunch catered by Farrell’s Restaurant in Portland (includes vegan option, water, soft drinks, desserts, etc) Served from Noon - 3:00PM
Lunch served at: Portland Riverfront Park, 284 Brownstone Ave, Portland, CT 06480
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Sat, Sep 12, 2026 at 8:15 AMSee full details
Stage 1/AirLine Cycles and friends are proud to bring you Belltown Throwdown 1, at the beautiful YMCA Camp Ingersoll. This is the first of two races hosted by Stage 1 at Ingersoll this year, but rest assured, the two races will be on 100% different courses… and we're not just doing the opposite direction move either! !
Want to help out? Sign up to volunteer here by sending us an email. We'll give you a t-shirt, some snacks and beverages, and unlimited high fives. https://www.signupgenius.com/go/10C0C49ABA629A75-57553048-belltown
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RACE DETAILS
BE SURE TO PREREGISTER -- DAY-OF REGISTRATION MAY NOT BE AVAILABLE!
We packed as much into this event as we could, and then we packed even more! Like all the AirLine and Stage 1 events, we want Belltown Throwdown 1 to be a fun day of racing AND spectating; that means a fun course full of our trade mark "special features", sweet music, and big prizes. We're also psyched to be part of the Project Mayhem CX series, which means consistent schedules, neutral support at every race, series prizes, and a cohesive calendar of great events.
What can you expect? A great course that will be equal parts fun and challenging. For example, this...
And this...
And this...
And, of course, plenty of this...
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What else? How about just $20 for each additional race!
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Just a couple of things to note about the event as you're planning to attend.
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All dogs must be kept on leash (6 feet or shorter). No exceptions. A loose dog is dangerous to itself and the racers.
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PRERIDING THE COURSE WILL BE AT THE DISCRETION OF THE OFFICIALS. THE COURSE MAY NOT BE OPEN FOR PRERIDING BETWEEN RACES. We tried to build time into the schedule to allow it, but there may not be time. All prerides must begin AFTER the finish line and you must check with the officials/volunteers at the officals tent to see if it is permitted at that time. If you are preriding, DO NOT PASS ANY ACTIVE RACERS. If you pass an active racer, we reserve the right to DQ you from your event and you will not get a refund. You have been warned.
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Sunrise is at 6:22am. Course will open for pre-ride at 6:30am and close at 8:10am. If you want to pre-ride for the morning session, show up early.
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In the interest of serving our racers, if you cannot attend we will refund you for any reason at any time up to registration closing. Email us. If you wanna make up a funny story, great.
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Want to help out? Sign up to volunteer here by sending us an email. We'll give you a t-shirt, some snacks and beverages, and unlimited high fives. https://www.signupgenius.com/go/10C0C49ABA629A75-57553048-belltown
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We are working on day-of registration. We CANNOT guarantee it, but we will try, so it is better if you register in advance. If we are able to do day of registration, there will be a $10 surcharge. Second race is available for $20 if you want to race multiple categories in a day.
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Staging will be based on: a. Top 8 from the series b. Cross-Results race predictor. c. Day of registrations
All mixed gender junior fields will be staged as follows: Top 8 (front row) will be 50/50 boys and girls by PMCX series standings. Rest of field will be mixed according to cross results race predictor.
Multiple Starts at the same time staging rules: We will be doing 1 minute gaps between fields with the caveat that we reserve the right to combine starts where either or both of them have 10 or less registrants. In that case, the front row will be split 4/4 and the rest of the field staged by crossresults.com race predictor.
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We will be providing FREE photos to racers. Look for photographer Bill Kurtz out on course throughout the day.
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Cash Prizes:
5 or fewer | $85 — $65 — $45
6 racers | $85 — $65 — $45
7 racers | $85 — $65 — $45 — $30
8 racers | $85 — $65 — $45 — $30
9 racers | $85 — $65 — $45 — $30 — $25
10 or more racers | $85 — $65 — $45 — $30 — $25
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Why are the Open and Womens P123 races different lengths? Don't you care about equality and equity? We do. So much so that we reached out to a handful of elite women to get their opinion, and based on that feedback we made this decision. Given the constraints of running a whole bunch of categories in the day, and wanting to give women separate time slots from men, what made the most sense for our schedule was to have the P123 women and the 40+ Women share the course and do 50 and 48 minutes respectively, instead of forcing them to race with the men. (we try to make as many people happy as possible. If you have scheduling suggestions for us that you think would work better, we are always happy to entertain them for next year)
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Belltown Throwdown CX, like all Stage 1 Cycling and AirLine Cycles events, is an inclusive race environment that is safe and welcoming to all participants, regardless of sex, sexual orientation, gender identity, age, race, religion, disability, or ethnic origin. Athletes are allowed to compete in the gender category that they identify as. Non-Binary athletes are welcome to compete in the Non-Binary category or any of the Open and Women categories.
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We strive to create an atmosphere that makes all feel welcome. From Pros to first-time racers, from staff to spectators, we will not accept behavior that is deemed to be bullying or any form of harassment and violators will be asked to leave.
At any point, if you feel uncomfortable or unsafe or see behavior that seems to be making someone else uncomfortable, please speak to an official or staff member.
- We've tried to get all planning done ahead of time, but sometimes things change for one reason or another (often outside of our control). Please be understanding and flexible with us. You can help us put on a great event by REGISTERING EARLY! We have to plan out porto-potties, food, shirts, porto-potties, registration staff, and even PORTO-LETS based on the expected registration…. so if you always register at the last possible second, you may have time to ponder all life's mysteries as you wait in long porto-let lines! To help encourage this, the first 50 registrants get a nice discount!
Pain in the Neck and the Project Mayhem CX Series are brought to you by:
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STAGE 1 CYCLING, INC.
"The Belltown Original"
Est. 1987
06424
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Sat, Sep 26, 2026 at 10:00 AMSee full details
Portland Come on Over 5K Race Information - Online Registration only
Date: Saturday, September 27, 2025, Rain or Shine
Start Time: 10:00 AM
Location: Portland Riverfront Park, 284 Brownstone Avenue, Portland, CT 06480
Awards: Medals will awarded to top 3 finishers in each age category for the in-person 5K
Register Online: Race Sign Up
In office or mail in to PO Box 71, Portland CT 06480
Bib #s and Timing: Race day 8:45-9:45 AM
Proceeds: Race proceeds benefit Portland Parks & Recreation Programs and Camp Scholarship Opportunities!
Inclement Weather: Portland Parks & Recreation Hotline- 860-262-7234
T-Shirts: Must register by September 1, 2025 to qualify for a free t-shirt.
Divisions for 5K :
12 and under,13 to 15,16 to 18,19 to 29
30 to 39, 40 to 49, 50 to 59, 60 to 64, 65 to 69, 70 and older
Online Registration only