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5 walking events in Stratford, Connecticut

From big races to Saturday morning group runs—find walking events and connect with the local endurance sports community.

  • YOUR BEST CHANCE FOR ROMANCE 3 Mile Run, or walk. [runsignup.com]

    Sat, Feb 14, 2026 at 9:15 AM

    Description

    NOT ONLY ARE WE BACK AT BOOTHE PARK...

    WE ARE ACTUALLY ON VALENTINE'S DAY! So it is YOUR 'BEST CHANCE!' for ROMANCE

    A couple of important reminders from the past-

    We will have a warm building to host...

    NOT ONLY ARE WE BACK AT BOOTHE PARK...

    WE ARE ACTUALLY ON VALENTINE'S DAY! So it is YOUR 'BEST CHANCE!' for ROMANCE

    A couple of important reminders from the past-

    We will have a warm building to host registration and pickup- but it is small.

    Come dressed to run, arrive early for parking (or you may have to 'hoof it'...)

    The 'challenge' of that wonderful Chapel St hill at the start of mile three returns!

    (But there's great downhill after that)

    We really need a minimum of 50 paid entries to hold this event. PLEASE register early.

    SATURDAY 2/14 WE ARE PLANNING FOR A GREAT RUN/WALK

    9:15AM FREE Kids Fun Run (ages 9 & under please)

    9:30AM START run/walk

    Reg opens 8 am 1/16-

    $30 for 19 & older

    $20 for 18 & under

    Increase on 2/9 -$35/$25

    THANKS TO THE SUPPORT OF THE STRATFORD POLICE, STRATFORD PARKS DEPT, STRATFORD DPW, OUR SPONSORS AND THE COOPERATIVE EFFORTS OF WONDERFUL VOLUNTEERS (you can be one too- there are a lot of races that need your help)

    In the past this event was designed to be after V-Day. But this year it worked out differently. Here's your chance to make up for any little “oversight” that may have occurred in the past!

    Run with a partner, a significant other, a spouse, or on your own spreading love and continuing the spirit of St Valentine.

    We do have a 150 person limit for this event. Please pre-reg early & don't get shut out.

    And while you are with us we hope you’ll join us and help donate to the Stratford Police Cadets. A terrific group of young men and women who want to help in our community and work in law enforcement.

    FEB 8th- Guaranteed swag ends- mugs & stuff - it all depends on costs, availability & tariffs!

    How can you get your name/business on our website & advertising? IT’S EASY!

    Donate $100 or more and you’re on! It’s a tax deductible donation right into the Stratford Police Cadets fund.

    You MUST contact Marty Schaivone and set this up. We really could use your help. Sponsors get a free entries too! msrunningproductions@yahoo.com

    SATURDAY 2/14 - 3 mile will start at 9:30am

    8:00am pickup starts for bibs, shirts or warm hats

    9:15am - We will have a safe, short-distance, non-competitive kids' fun run if weather permits and there are any kids (9 and under only). You can accompany your little tyke to avoid potential drama. (Theirs or yours!).

    **Kids run is directed by Donna Cramond- former professional cat herder & certified Bon Vivant.

    930am- Start of 3 mile event which is timed - everyone is eligible for awards. Jim Gerweck is our official Race Timer.

    9:45am- Hot soup! Snack bars/wrapped snacks, bananas, water.

    ONLINE REGISTRATION ONLY- even on race day

    $30 for pre-reg 19 & over through 2/8. Just $20 for 18 & under

    $35 / $25 from 2/9 - Feb 14

    WE CAN NOT PROCESS ANY PAPER NOR TAKE CASH ON RACE DAY- only online reg. Bring your phone!

    ONLINE REGISTRATION IS OPEN UNTIL 9:30am RACE MORNING - UNLESS WE ARE SOLD OUT (150 runners)

    PRIZES- likely edible and tasty and medals for the younger age groups. There may be gift cards as well.

    Overall male & female & NB champions WILL GET AWARDS OF SOME SORT, might even be edible...

    Two deep in age groups- 9 & under, 10-13, 14-18, 19-29, 30-39, 40-49, 50-59, 60-69, 70-79 & older if they’re pre-registered.

    **HOLD ONTO YOUR BIB-it may be worth a discount somewhere- we will let you know...

    Prizes for the top 2 person team based on cumulative ages.

    Teams for each category are eligible- M&F, M&M, F&F, NB&NB

    Combined age groups- 60 & under, 61-75, 76-100, 101-125, 126-150, 151+

    What are the awards? They might be edible- that's the best kind. Medals and trophies can chip your teeth.

    You can run, walk or stroll this event as an individual- you do NOT need a partner.

    PLEASE HELP US RECRUIT PARTICIPANTS! We need a minimum of 50 people to be able to hold this event

    PLEASE REG BY FEB 1st so we can make sure you get you the mugs and maybe Socks? Hats?

    Sat 2/14 PICKUP at Boothe Park STARTS 8:00am and the 3 miler starts at 9:30am

    OUR LOCATION is at the Boothe Memorial Park building-

    5800 Main Streat in the Putney (North End) section of Stratford

    COURSE MAP https://onthegomap.com/#/route/019bd28f-e8d6-7023-a698-756d65fe2754

    NOTE- there is no water table on the course- please carry your own if needed.

    With fixed costs and pre-payment of many items, this means we CANNOT, under any conditions, REFUND any registration fees. Whether we are live or virtual our commitment to our Police Cadetss will be maintained. We hope you can support this commitment and join us.

    IMPORTANT DETAIL- We encourage everyone to donate any additional amount to the Stratford Police Cadets. Your donation goes directly to the cadets and is not used for any event costs. It is a 501c3 and fully tax-deductible.

    WE NEED YOUR HELP FOR A SAFE START- If you are truly at a speedier running level (6-7min pace per mile or under) we urge you to be at the start early and ready to go at 9:30am. This will avoid crowding on the course and help everyone to run more safely. Thanks!

    You can push a baby stroller but must start towards the back of the pack, have at least some sort of mammal in the stroller, and not curse as you fly down the hills and then have to climb that big hill, pushing the stroller...

    ON THE COURSE- We ask you to stay safe, don’t run in groups…watch for traffic.

    Race Director and slightly crazed Founder who really should retire

    Marty Schaivone, with 35 years of experience, will coordinate this event. MS Running Productions has directed & consulted on more than 30 races every year in CT including other races in Stratford- the Little O'Pub, Miles for Margaritas, Christmas in July Surfin Santa, Two Roads Shore to the Pour, Happy HalloWINE, the Turkey Trot, Holiday Toy Run and !/2 way to St Pats 5k. Also the Great Pumpkin Classic in Trumbull, the Beach Bunny 5k, Bigelow Tea Community Challenge & Colony Grill Hot Oil in Fairfield, and many others in Milford, Bridgeport, Westport, and beyond.

    Last year MSRP was involved with events that contributed over $250,000 to local charities.

    Contact Marty at msrunningproductions@yahoo.com for terrific opportunities to sponsor this event or to volunteer at this run as well as any others. The very modified and constantly changing 2026 schedule (if it ever happens) will be posted at www.hitekracing.com/msrunning.com

    FAQ’s

    Is there valet parking? Yes, that will be available when pigs can fly.

    Is the course marked clearly and accurately? If you get lost on this course we will refund your money, someday. And if you run long by accident we will not charge extra. It is a 3 mile loop with basically four, right hand turns. There will be signs, cones, flour arrows on the road and police on the course.

    Is Boothe Park actually named after the Toll Booths in the back lot? NO- besides being spelled differently the toll booths came after the park was formed. They were brought directly from the nearby Merritt Parkway. We used to throw dimes, then quarters into them whenever crossing the Sikorsky Bridge on the Merritt.

    How can I get my name/business on the website? IT’S EASY!

    Donate $100 or more and you’re on! It’s tax deductible right into the Stratford Police Cadets.

    You MUST contact Marty Schaivone and set this up. We really could use your help. Sponsors get a free entry and the two race shirts! msrunningproductions@yahoo.com

    Why is it 3 miles and not 5k?

    First off- trying to add on another 1/10 mile would have caused logistical problems, messed up the start/finish, and been annoying.

    Secondly- I never did well using the metric system despite being a Science Major.

    Thirdly- Since there are no other 3 milers around this will become a unique PR for you. You're welcome!

    3 Miles Run Walk

    5800 Main St, Stratford, Connecticut, 06615, United States
    OpenStreetMap Google Maps
  • THE LITTLE O’PUB 5K [runsignup.com]

    Sun, Mar 15, 2026 at 9:45 AM

    Description

    Just a wee bit early but our ST. PATS RUN IS BACK!

    We have a strict limit of 250 human participants.

    It’s a couple of days BEFORE St Patrick’s and it’s time to roll out of bed and get up for a little...

    Just a wee bit early but our ST. PATS RUN IS BACK!

    We have a strict limit of 250 human participants.

    It’s a couple of days BEFORE St Patrick’s and it’s time to roll out of bed and get up for a little

    “PRE PARTY” activity. We all need the proper warmup for Tuesday!

    You might want a little caloric burn-off help (excuse) to consume the corned beef and ales-

    So join us!

    Run/walk off those calories BEFORE St Patrick's AND bring some friends to make it easier!

    Three years ago we hosted “The Hair of the Dog” 5K - the day AFTER St Patrick's.

    But with St Pats on a Tuesday we are in 'pre-St.' mode.

    Our small ‘boutique’ 5K event is hosted by the Little Pub in the Lordship section of Stratford.

    It will feature some amenities you don’t often find in a local run as part of the package.

    This event was created by the overly active minds which brought you Miles for Margaritas,

    the Surfin' Santa, HalloWINE 5K, and the "Half Way to St Pat's Day" last Sept.

    HERE ARE YOUR INCENTIVES - POST RUN!

    *LUCKY LAGER to participants 21 & over *

    *Irish Whiskey shots

    *Great snacks & fluids

    *N/a ATHLETIC BREW craft brew & soft drinks

    Special Tshirt design * (Size guarantee & availability ends 3/4)

    Our very scenic & flat out ‘n’ back course along the water*

    Accurately timed results**

    *Special discounts inside LITTLE PUB for further camaraderie

    (you'll love their Bloody Mary's)

    AND we will list more as they come in.

    Event fees- limited to 250 participants

    1/17- 1/31 $30 for 21 & over, $25 for 20 & under (note cc fees above)

    2/1-3/8 $33 for 21 & over, $25 for 20 & under stays the same

    3/9-3/15 $36 / $25

    Event calendar

    1/17 Registration opens - Get 'er done before we sell out like we did last year.

    3/4 Shirt size guarantee ends (we may run out after that)

    3/14 8:30-10:30am Early bib & swag pickup @ Little Pub

    Celebrate St Pats EARLY @ LITTLE PUB BRUNCH

    3/15 8:30 am Bib & swag pickup

    9:45 am Little tykes ‘free-leaf’ clover scamper- directed by Donna Cramond!

    10:00 am START of the 5K

    SNACKS, ALE, Non Alc beverages,

    Crazy/fun AWARDS to follow including holiday themed socks & stuff

    AWARDS - M/F & NG champs get $25 Little Pub gift cards.

    1st & 2nd Age group awards 9 & under, 10-13, 14-18, 19-29, 30-39, 40-49, 50-59, 60-69, 70+ (80’s if pre-reg)

    GIFT CARDS FROM MARATHON SPORTS, DROWSY WHALER**, & MORE

    *SAVE YOUR BIB- BRING TO THE DROWSY WHALER THROUGH MARCH 31

    & GET 10% OFF YOUR ORDER!

    *Located at 1 Dorne Dr, the entrance to Short Beach & the Par 3 course

    HUGE THANKS TO OUR HOST THE LITTLE PUB

    with Doug Grabe & Jillian Bass!

    THANKS ALSO to the cooperation of the Stratford Police, DPW and Recreation departments.

    Race Coordinator - Marty Schaivone directs over 30 events each year including six others in Stratford,

    & many more in Trumbull, Fairfield and other towns in the area.

    Parking - Plenty along the seawall and in the Little Pub lots. But get here EARLY

    Valet Parking Available - Bring your own driver!

    *Shirt info- T-shirt type, color, & fabric is subject to cost, availability, any tariffs by the Pres,

    and the whim of the Race Director (who is known to be very whimsical)

    ** COURSE MAP https://www.plotaroute.com/route/2396355

    ***If your time is not what you expected just print it on a $20 bill and give it to our timer.

    THIS IS FROM 2023 when we hosted the "Hair of the Dog" 5k -

    For those who desperately seek more information (or never heard the expression ’Hair of the Dog’),

    What does hair of the dog mean?

    A morning drink may be the last thing you want after a night of boozing, but that’s exactly what this quirky English expression means. Originally, the expression referred to a method of treating a rabid dog bite; hair from the dog was placed in the wound. So in that sense, having another drink (any drink) is like taking hair from the dog that bit you.

    (By the way, medical professionals do not prescribe alcoholic drinks to treat the symptoms of a hangover. However, they do encourage drinking water and getting rest.)

    What about the Bloody Mary?

    Many suffering from the morning-after blues indulge in a Bloody Mary as a hangover cure. This savory cocktail contains vodka, tomato juice, and other flavorings such as horseradish, celery salt, lemon juice, and Tabasco sauce.

    There are as many versions of the Bloody Mary as there are theories regarding who the drink is named after, with beliefs ranging from Queen Mary I, to the actress Mary Pickford, to a waitress in Chicago who worked at a bar called the Bucket of Blood.

    5k Run Walk

    10 Washington Parkway, Stratford, Connecticut, 06615, United States
    OpenStreetMap Google Maps
  • Boston Blowout- Spring Fling 3/22/2026 [runsignup.com]

    Sun, Mar 22, 2026 at 8:00 AM

    Description

    THE BLOWOUT IS BACK IN LORDSHIP! Sunday March 22

    STAY FOR BRUNCH AT THE LITTLE PUB RESTAURANT

    NOTE- ONCE WE HAVE REACHED OUR 50 MINIMUM WE CAN PROCEED FULL SPEED AHEAD FOR THE BLOWOUT

    We’ve got...

    THE BLOWOUT IS BACK IN LORDSHIP! Sunday March 22

    STAY FOR BRUNCH AT THE LITTLE PUB RESTAURANT

    NOTE- ONCE WE HAVE REACHED OUR 50 MINIMUM WE CAN PROCEED FULL SPEED AHEAD FOR THE BLOWOUT

    We’ve got room/permitted for up to 150 so tell your friends, spread the word, post it on social media. We will be ready to go for this unique, 10K loop in the scenic, quiet and pretty darn flat, hamlet of Lordship.

    Our partner Little Pub has a terrific brunch starting at 10am. Bring a change of clothes and join us. You’ll certainly work up an appetite from your run!

    If you plan to enjoy brunch- head right in from 10-3. The LP does not take reservations.

    THE COURSE - our loop is 6.2 miles of flat and scenic roads.

    THE GOOD NEWS…

    We are running through the wonderfully scenic section of Stratford, along the water. It’s a pretty darn quiet neighborhood and really flat. We start and finish in the lot area across from the Little Pub at 10 Washington Pkwy.

    It is a great place to do a long run on your own or with some friends.

    Run/walk 6.2, 12.4, or 18.6 miles*. There will be at least one or two water tables on the course and plenty at the start/finish.

    BUT it’s always a good idea to carry your own water or plant some ahead of time.

    For those that are really into marathon training distance- you can easily add on miles before or after!

    TAKE YOUR PICK OF DISTANCE

    The finish line will remain open until noon (That's around a 12+ min. pace if you start the 30k at 8:00am).

    If you plan to run a bit slower please email our Director to start earlier. IF YOU ARE STARTING EARLY You must connect with our timer JIM - before you start! jimrg156@gmail.com

    The course is well marked with signage, cones and flour arrows on the streets. Course maps will be available and the link will be here soon.

    (you can even change to a shorter distance while you’re in it!)

    We have designed a great 6.2 mile loop course that you can run once, twice or thrice. With our safe, flat loop you’ll be able to maintain a consistent pace of your choice. We offer you a low-key event to keep costs down, but still have a quality run and enjoy the experience.

    HERE IS OUR PROPOSED COURSE- https://onthegomap.com/#/route/019bf7fc-130a-717d-96d9-7c411ee6b857

    IT COULD BE RUN IN REVERSE IF WE DETERMINE THE WIND IS OBNOXIOUS IN ONE DIRECTION- ESPECIALLY ALONG THE BEACH OR THE WATER.

    We always hear “There are no 10K's in CT anymore!” Now there is one to try.

    It will be well marked on quiet roads. There is a warm restaurant to come back to if you decide to 'brunch' with us or even just enjoy a post run beverage of your choice.

    If you feel great & decide to extend your run for another loop- go for it!

    There's only a couple of other 20k's, and no other 30K's in CT that we know of.

    This is a great opportunity to try any of the distances without any pressure. It’s a great training run for a future half marathon, marathon, or just to show yourself it is possible. It’s also a chance to run a PR if you’re ready.

    OUR 10K LOOP COURSE - https://onthegomap.com/#/route/019bf7fc-130a-717d-96d9-7c411ee6b857

    TIMING- JIM GERWECK! will use chip timing so you will get a 'net time' since there is a common start/finish line. And if you really need to start later than the 8:15am official start, Jim can accommodate you. (Remember- always write your name and time you wanted to run on a $20 bill* and Jim can help you get your best time)

    AND WE URGE YOU TO ALSO PLEASE KEEP YOUR OWN TIME AS A BACKUP. We want to make sure every possible safeguard is in place. THANKS!

    SWAG- We will have something for you - a shirt, hat, socks...depending on the tariffs and whether Musk has fired either Jim or Marty. Put in your shirt size just in case... socks and hats are uni-sized.

    EVENT DAY SCHEDULE 3/22/26

    5:30am Wake up, carefully roll out of bed & turn on the coffee

    6:00am Get semi-dressed, try not to pull a muscle

    7:00am Start driving if you're within 30 miles. If any farther you're late

    7:15am Bib distribution starts- Bring your own pins b/c you probably have a lot from the other races!

    7:55am Last call for the porto-pot ?

    8:00am Start of the 10k/20k/30k (or more on your own if you want)

    Snacks, fluids, surprises when you are done.

    10:00am BRUNCH STARTS at the Little Pub- It's Good Eatin' and a great view!

    WE WILL HAVE SOME SORT OF SWAG AND EVEN SOME AWARDS. We are not quite sure what they will be, yet.

    If you can't stay for brunch at least plan to stop in LITTLE PUB for some well needed hydration!

    IT'S MARCH MADNESS! The GAMES ARE ON!

    Volunteers are always welcome - if you have friends or family that could help us with food, fluids, water tables, course marshal, etc. PLEASE EMAIL Marty- msrunningproductions@yahoo.com

    Thanks again! Marty Schaivone - Race Director

    Jim Gerweck - Timing Director

    *Could be subject to increase based on gas prices

    10k 20k 30k Run Walk

    Stratford, Connecticut, 06615, United States
    OpenStreetMap Google Maps

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