May 2027 bike rides & races

Dates

Sat, May 1, 2027

Where

Oak Bluffs (Martha's Vineyard), MA

Distances

25, 45, 60 mi

Format

Bike MS ride (one-day)

Cause

MS — National Multiple Sclerosis Society

Min. fundraising

$250

Organizer

National MS Society

Registration

2027 registration opens Sep 2026

DateEvent page: 'Join us next year - Saturday, May 1, 2027' (registration opens September 2026). 2026 was May 2.

Event siteSources: events.nationalmssociety.org events.nationalmssociety.org

Dates

Sat, May 1 – Sun, May 2, 2027

Where

Fort Worth, TX

Distances

35 and 75 mi (optional loop to 100)

Format

Bike MS ride (two-day)

Cause

MS — National Multiple Sclerosis Society

Min. fundraising

$300

Organizer

National MS Society

Registration

2027 save-the-date posted

DateEvent page: 'Next year's Bike MS: Round-Up Ride is scheduled for May 1-2, 2027.' 2026 was May 2-3.

Event siteSources: events.nationalmssociety.org

Dates

Sat, May 1, 2027

Where

Redlands, CA

Distances

113 mi / 12,200 ft (timed 74 mi to summit) or 81 mi / 8,900 ft (timed 43 mi)

Elevation

12,200 ft (full) / 8,900 ft (short)

Format

timed climb Redlands to Onyx Summit (8,443 ft); Quadzilla stage 2

Organizer

Planet Ultra Inc

Registration

Opens Dec 24, 2026; $154.08 (+$10 last-minute)

DatePlanet Ultra: May 1, 2027 (2026 edition was May 2, 2026).

NotesChip-timed start to summit; riders may arrange pickup instead of descending.

Event siteSources: planetultra.com bikesignup.com

Dates

Sat, May 1 – Mon, May 3, 2027 · projected (2026 was May 2–3)

Where

Moab, UT

Distances

~50 mi road/gravel fondo (longer road loop historically ~60 mi / 6,000 ft)

Format

timed road (and gravel) fondo, La Sal Loop

Organizer

TransRockies

DateDate not confirmed yet. Check the organizer’s site.

Event siteSources: cyclingwest.com

Dates

Sat, May 1 – Mon, May 3, 2027 · projected

Where

Moab, UT

Distances

Stage 1 Porcupine Rim 22.5 mi; Stage 2 Klondike Bluffs 25.5 mi; Stage 3 Mag 7 28.5 mi (76 mi / 7,800 ft); 350-rider cap

Format

3-day MTB stage race

Organizer

TransRockies

Series

TransRockies Race Series (Moab Fondo Fest weekend)

Lottery

No lottery.

Date2026 ran the same first-weekend-of-May slot.

Event siteSources: strambecco.com strambecco.com

Dates

Sat, May 1, 2027

Where

Creston, CA

Distances

35, 50, 65, 80, 100 mi

Elevation

2,300 ft (35 mi) to 5,500 ft (100 mi)

Format

club century, Paso Robles wine country

Cause

Bike SLO County and local cycling/community groups

Organizer

San Luis Obispo Bicycle Club

Registration

Not yet open; 700-rider cap (sells out)

Dateslobc.org/wildflower lists May 1, 2027 (page updated Aug 15, 2026). 2026 edition was April 18, 2026.

Event siteSources: slobc.org socalcycling.com

Dates

Sat, May 1, 2027

Where

Santa Rosa (Luther Burbank Center), CA

Distances

100 mi, 100 km, 28 mi

Format

Sonoma County club century (SRCC)

Cause

Bike advocacy — Various local causes

Organizer

Santa Rosa Cycling Club

Registration

Opens early 2027 (historically sells out quickly)

Datewinecountrycentury.com and srcc.com: May 1, 2027 (2026 edition May 2, 2026).

Event siteSources: winecountrycentury.com srcc.com

Dates

Sun, May 2, 2027

Where

Temecula, CA

Format

Temecula wine-country ride

Registration

Listed

NotesMinor event.

Sources: findarace.com

Dates

Sun, May 2, 2027 · projected (2026 was May 3)

Where

Moraga (Campolindo High School), CA

Distances

52, 76, 102, 110 mi

Format

hilly East Bay club century (Grizzly Peak Cyclists)

Organizer

Grizzly Peak Cyclists

Date2026 edition Sun May 3, 2026 (first Sunday of May). 2027 projected May 2.

Event siteSources: danshryock.substack.com bikeeastbay.org

Dates

Sun, May 2, 2027 · projected (2026 was May 3)

Where

Seattle, WA

Distances

Long and short route options

Format

community ride with long and short routes

Cause

Children — Cascade Bicycle Club Major Taylor Project

Organizer

Cascade Bicycle Club

Registration

2027 registration not yet open as of Sept 2026

DateNo 2027 date published. 2026 was Sun May 3, 2026 (first Sunday in May); first Sunday of May 2027 = Sun May 2, 2027.

NotesPrimarily a riding event; proceeds support the Major Taylor Project youth program (incidental beneficiary).

Event siteSources: cascade.org cascade.org

The town

Once you’re in Seattle

SleepHotels in Seattle5 picks · ask about the bike when you book EatRestaurants in Seattle6 picks, night before and after FixBike shops in Seattle4 shops · 2 rent bikes

The Seattle town guide →

Dates

Sun, May 2, 2027

Where

New York, NY

Distances

40 miles (five boroughs, car-free)

Format

car-free mass-participation city ride

Cause

Bike New York free bike-education programs (registration includes tax-deductible donation)

Organizer

Bike New York

Registration

Open since Sept 15, 2026; Standard and Bike New York member $187.12 (includes a $36 tax-deductible donation), VIP $496.70; Team Bike New York fundraisers need $650 by Apr 15, 2027; 2027 charity-partner applications are closed.

DateOfficial site: 'SUNDAY, MAY 2, 2027'; registration opens Tuesday Sept 15, 2026.

Notes~32,000 riders; historically sells out.

Event siteSources: bike.nyc bike.nyc

The town

Once you’re in New York

SleepHotels in New York4 picks · ask about the bike when you book EatRestaurants in New York4 picks, night before and after FixBike shops in New York4 shops · 2 rent bikes

The New York town guide →

Dates

Fri, May 7, 2027 · projected (2026 was May 8)

Where

Tucson, AZ

Distances

56 mi round trip (21 mi climb / 21 mi descent)

Elevation

6,600 ft gain, avg 4.5% (ranked 33rd toughest US road climb)

Format

supported club hill climb, 21-mile climb to Summerhaven

Organizer

Greater Arizona Bicycling Association (GABA)

Registration

2026 closed; 2027 not yet open

Date2026 edition ran Friday May 8, 2026 (registration now closed). That matches the 2nd-Friday-of-May pattern. Not organizer-published.

NotesStart McDonald District Park; 4 SAG stops incl. pie at the top.

CheckNot checked with the organizer yet. Look at their site before you plan around it.

Event siteSources: bikegaba.org granfondoguide.com

The town

Once you’re in Tucson

SleepHotels in Tucson5 picks · ask about the bike when you book EatRestaurants in Tucson6 picks, night before and after FixBike shops in Tucson5 shops · 2 rent bikes

The Tucson town guide →

Dates

Sat, May 8, 2027

Where

Cable, WI

Distances

100, 60, 28 miles ($49)

Format

CAMBA gravel race

Cause

Bike advocacy — Chequamegon Area Mountain Bike Association

Organizer

CAMBA

Registration

Open (BikeReg).

Lottery

No lottery.

DateRegistration opened May 28, 2026 (bikereg.com/hungrybear100).

Event siteSources: gravelcalendar.com

Dates

Sat, May 8, 2027

Where

Lone Jack, MO

Format

Missouri gravel race

Organizer

Muleskinner Gravel

Lottery

No lottery.

Event siteSources: gravelcalendar.com

Dates

Sat, May 8 – Sun, May 9, 2027 · projected

Where

Santa Fe, NM

Distances

Century, gran fondo and half-century options; road and gravel events

Format

classic northern New Mexico century (with gravel fondo)

Organizer

Santa Fe Century

DateDate not confirmed yet. Check the organizer’s site.

Sources: cyclingwest.com

Dates

Sat, May 8, 2027

Where

Chattanooga, TN

Distances

~30 mi (Mocktail), ~50 mi (IPA), 100 mi (White Dog), 'Old Fashioned', 132 mi (The Four Horsemen)

Format

multi-distance road ride/race (up to 132 mi)

Organizer

Scenic City Cyclo (organizer not named on listing)

DateNot checked with the organizer yet. Look at their site before you plan around it.

Event siteSources: findarace.com findarace.com

Dates

Sat, May 8, 2027 · projected (2026 was May 9)

Where

Burlington / Mount Vernon (Skagit Valley), WA

Distances

Multiple routes including metric and full century options

Format

spring century

Organizer

Skagit Bicycle Club

Registration

2027 registration not yet open as of Sept 2026

DateNo 2027 date published. The 34th annual edition was Sat May 9, 2026; projecting the corresponding second Saturday in May 2027 = Sat May 8, 2027.

NotesRolling farm roads of the Skagit Valley; 34th annual edition ran in 2026.

Event siteSources: visitskagitvalley.com skagitbicycleclub.org

Dates

Wed, May 12 – Sun, May 16, 2027

Where

Bentonville, AR

Distances

115 mi main, 60 mi, 35 mi (route released close to race day)

Format

three-surface (road/gravel/singletrack) race + festival

Organizer

Rule of Three LLC (founded 2021 by Allied Cycle Works team)

Registration

Opens Feb 1, 2027; ~650 riders.

Lottery

No lottery.

DateOrganizer site: 'May 12–16, 2027', registration opens Feb 1, 2027; race day Saturday May 15, 2027.

NotesCompanion events: Rule of $3.99 (Jan 9, 2027) and Hazel Valley Rally (Apr 10, 2027).

Event siteSources: ruleofthree.bike gravelgodcycling.com

Dates

Thu, May 13 – Sun, May 16, 2027

Where

Sacramento (Beals Point, Folsom Lake), CA

Route

Beals Point (Folsom Lake) → Sacramento (State Capitol steps)

Format

HIV/AIDS multi-day (4-day, Sacramento area)

Cause

HIV/AIDS — AIDS service organizations across Sacramento and Greater Northern California

Min. fundraising

$2,000 for cyclists; $600 for crew

Organizer

NorCal AIDS Cycle (Sacramento)

Registration

Open; registration and fundraising page live.

DateEvent page (charity.pledgeit.org/NCAC, checked Oct 1, 2026): May 13-16, 2027. Day 1 starts at Beals Point with basecamp at the Yuba-Sutter Fairgrounds for Days 1-3; Day 4 returns to the Capitol steps in Sacramento.

NotesNewly listed. Finishes five days before Cycle to Zero starts (May 21). Contact on the page: ncaceventinfo@gmail.com.

Event siteSources: charity.pledgeit.org

Dates

Thu, May 13, 2027 · projected (2026 was May 14)

Where

Flagstaff, AZ

Distances

~400 mi (course changes each year)

Format

self-supported northern Arizona race

Organizer

Dana Ernst and Dylan Turner

Registration

No formal registration

Qualification

None (self-supported)

Date2026 start Thu May 14, 2026, 6am from Flagstaff Bicycle Revolution; course changes yearly. 2027 projected to the equivalent mid-May Thursday (May 13, 2027); not yet announced.

Event siteSources: bikepacking.com

Dates

Sat, May 15, 2027 · projected (2026 was May 17)

Where

Springfield, OH

Distances

12-hour and 6-hour timed races (24-hour edition listed for 2026); flat 7-mile loop course

Format

12-hour / 6-hour (and 24-hour) timed road race

Organizer

Calvin's Challenge (Ohio ultra community)

Registration

Not yet open for 2027

Qualification

Open entry

DateThe event traditionally runs on a mid-May Saturday in Springfield, OH. 2027 date projected to Sat May 15, 2027; not yet announced.

Sources: ultracycling.com ultracycling.com

Dates

Sat, May 15 – Sun, May 16, 2027 · projected

Where

Jacksonville, AL

Distances

44, 62, 84, 100 miles and 126-mile ULTRA (13,385 ft)

Elevation

Up to 13,385 ft (ULTRA); 9,714 ft (100 mi)

Format

mountain gran fondo to Alabama's highest point

Organizer

Northeast Alabama Bicycle Association (NEABA)

DateGFNS partner page lists 'May 2026'. Event traditionally runs the third weekend of May (ULTRA Saturday, main rides Sunday).

NotesAlso a UCI Gran Fondo World Series qualifier in recent years.

CheckNot checked with the organizer yet. Look at their site before you plan around it.

Event siteSources: strambecco.com granfondonationalseries.com

Dates

Sat, May 15, 2027

Where

Davis, CA

Distances

200 mi (Yolo/Napa/Lake counties; 4-mile hard-pack dirt section)

Elevation

~9,000 ft

Format

Cal Triple Crown double (oldest continuously run double)

Organizer

Davis Bike Club

Registration

2027 not yet open; 2026 fees $140-$220

Datedavisbikeclub.org: next event May 15, 2027; Cal Triple Crown calendar agrees.

Notes2026 edition had 201 finishers.

Event siteSources: davisbikeclub.org caltriplecrown.org

Dates

Sat, May 15, 2027 · projected

Where

Henefer, UT

Distances

40 and 60-mile route choices

Format

gran fondo with two route options

DateDate not confirmed yet. Check the organizer’s site.

Sources: cyclingwest.com

Dates

Sat, May 15 – Sun, May 16, 2027 · projected (2026 was May 16–17)

Where

Red Wing (Lake Pepin loop), MN

Distances

~45 mi/day around Lake Pepin (MN/WI)

Elevation

rolling

Format

two-day vintage 3-speed tour (capped)

Organizer

The Lake Pepin 3-Speed Tour

Registration

$30; capped at 130 riders

DateProjected: 3rd weekend of May (2026 edition May 16-17, 2026). No 2027 date published.

NotesLycra-free, 3-speed bikes only.

Event siteSources: 3speedtour.com 3speedtour.com

Dates

Sat, May 15, 2027 · projected

Where

Loudonville, OH

Distances

100 mi and 100K

Format

NUE 100-mile MTB race

Organizer

Mohican 100

Series

NUE Series

Lottery

No lottery.

DateDate not confirmed yet. Check the organizer’s site.

Event siteSources: strambecco.com

Dates

Sat, May 15, 2027 · projected (2026 was May 16)

Where

Cottage Grove, OR

Distances

92 miles (Gran) and 62 miles (Medio)

Elevation

Substantial - all-road routes into the Coast Range foothills south of Eugene

Format

timed gran fondo

Cost

TBA

Organizer

Mudslinger Events (director Mike Ripley)

Registration

2027 registration not yet open as of Sept 2026. 2026 pricing: $130 early / $140 after Jan 2 / $150 after Apr 29. Registration via BikeReg.

DateThe organizer's page lists the 2027 edition as 'TBD 2027' - no date announced. The 2026 edition was Sat May 16, 2026; the event runs on a mid-May Saturday, so Sat May 15, 2027 is the projection.

NotesRound #5 of the Oregon Triple Crown Series. Start at Bohemia Park, Cottage Grove (~20 min south of Eugene). Timed with early-start option 30 minutes before the main wave; custom awards across 11 divisions.

Event siteSources: mudslingerevents.com granfondoguide.com

Dates

Sat, May 15, 2027 · projected (2026 was May 16)

Where

multiple valley start points to Pacific City, OR

Distances

Multiple start points giving roughly 25, 55, 80 and 100+ mile options, all finishing at the coast

Elevation

Coast Range crossing on the longer routes

Format

coast-bound charity century

Cause

Lung — American Lung Association

Organizer

American Lung Association

Registration

2027 registration not yet open as of Sept 2026

DateNo 2027 date published. The 2026 edition was Sat May 16, 2026 per both the Salem Bicycle Club and Portland Bicycling Club event calendars; the ride is held on a mid-May Saturday, so Sat May 15, 2027 is the projection.

NotesIt is nevertheless one of Oregon's largest one-day organized rides, with riders converging on Pacific City from several inland start points.

CheckNot checked with the organizer yet. Look at their site before you plan around it.

Event siteSources: portlandbicyclingclub.com salembicycleclub.org

Dates

Sat, May 15, 2027 · projected (2026 was May 16)

Where

Foxboro, MA

Distances

25, 50, 100 mi

Format

children's charity one-day ride

Cause

Children — Massachusetts youth-serving social-service agencies (Rodman Ride matches 10%)

Min. fundraising

Not published yet

Organizer

Rodman for Kids

Date2026 ride: Sat May 16, 2026 (third Saturday of May, Foxboro MA); projected to Sat May 15, 2027.

CheckNot checked with the organizer yet. Look at their site before you plan around it.

Event siteSources: bikenewengland.com

Dates

Sat, May 15, 2027 · projected

Where

Encinitas (Cardiff), CA

Distances

25, 37, 66, 103 mi

Format

North County coastal century (MiraCosta College start)

Organizer

San Diego Century

Registration

$80-$120

DateDate not confirmed yet. Check the organizer’s site.

Event siteSources: granfondoguide.com letsdothis.com

Dates

Sat, May 15, 2027 · projected

Where

Carson City, NV

Distances

Long/short gravel routes

Format

gravel race (Pete Stetina)

Organizer

Stetina's Paydirt

Lottery

No lottery.

DateDate not confirmed yet. Check the organizer’s site.

Event siteSources: strambecco.com

Dates

Sat, May 15 – Sun, May 16, 2027 · projected (2026 was May 16–17)

Where

Chillicothe, OH

Distances

Sat 58/68/93/100 mi; Sun 50/65/75/100 mi; 34-mi Paint Creek Trail option

Elevation

rolling

Format

two-day tour (hub format since 2026)

Organizer

Outdoor Pursuits (Columbus Outdoor Pursuits)

Registration

2026: $150 weekend online / $160 on-site / $95 single day; cap 2,000

DateProjected: 3rd weekend of May (2026 edition May 16-17, 2026). Organizer has not published 2027 dates.

NotesOldest continuing tour in US (since 1962). Format changed: no longer Columbus-Portsmouth; now loops from Yoctangee Park, Chillicothe.

Event siteSources: outdoor-pursuits.org granfondoguide.com

Dates

Sat, May 15, 2027

Where

Bothell (The Park at Bothell Landing), WA

Distances

Multiple route options (typically ~10–100 mi)

Format

diabetes one-day ride

Cause

Diabetes — American Diabetes Association

Min. fundraising

Fundraising minimum varies by route (check event page)

Organizer

American Diabetes Association

Registration

2027 event page live on diabetes.org

Datediabetes.org: Saturday May 15, 2027.

Event siteSources: diabetes.org

Dates

Sat, May 15, 2027 · projected (2026 was May 16)

Where

Orange City, IA

Distances

21 or 33 mi

Elevation

rolling

Format

Tulip Festival ride

Organizer

Orange City Chamber of Commerce

Registration

2026: $40

DateProjected: Saturday of the Orange City Tulip Festival, 3rd weekend of May (2026 edition Saturday May 16, 2026). No 2027 date published.

Event siteSources: bikeiowa.com

Dates

Sat, May 15, 2027 · projected (2026 was May 16)

Where

Washington, DC start, VA

Distances

562 mi (904 km) to Damascus, VA; mixed gravel/singletrack

Format

self-supported DC-to-Damascus race

Organizer

Trans Virginia organizers

Qualification

None (self-supported)

Date2026 start Sat May 16, 2026 from Washington, DC (bikepacking.com listing). 2027 projected to the equivalent mid-May Saturday (May 15, 2027); not yet announced.

Sources: bikepacking.com

Dates

Sat, May 15, 2027 · projected (2026 was May 16)

Where

De Beque (High Lonesome Ranch), CO

Distances

2027: Mustang 100 mi, Gunslinger 75 mi, Hoedown 30 mi; 2026 was 65/30

Format

ranch-country gravel race

Organizer

Gemini Adventures (previously Outside Events / Roll Massif)

Registration

~$105; free camping.

Lottery

No lottery.

Date2026 was May 16. Organizer lists 2027 courses expanded to 100/75/30 mi.

Event siteSources: strambecco.com gravelgodcycling.com

Dates

Sun, May 16, 2027 · projected (2026 was May 17)

Where

La Push, WA

Distances

690 mi (1,110 km) Pacific Ocean to Idaho border, mostly off-road

Format

self-supported cross-state race

Organizer

Troy Hopwood

Registration

No fee

Qualification

None (self-supported)

Date2026 start Sun May 17, 2026, 7am from First Beach, La Push. Traditionally a mid-May Sunday; 2027 projected Sun May 16, 2027. Not yet announced.

Event siteSources: bikepacking.com

Dates

Sun, May 16, 2027

Where

Chatham, NY

Format

Hudson Valley gravel race

Organizer

Farmer's Daughter

Lottery

No lottery.

Event siteSources: gravelcalendar.com

Dates

Sun, May 16, 2027

Where

New York, NY

Distances

Long (~100 mi) and Medium routes; start on George Washington Bridge, finish Fort Lee NJ

Format

gran fondo (timed, UCI-style)

Organizer

Gran Fondo New York Inc. (GFNY)

Registration

Open; early pricing $295 through May 4, 2027

DateOfficial site: 'MAY 16, 2027 World Championship New York City'. (2026 edition was May 17, 2026.)

NotesFlagship of the GFNY series; thousands of riders from 90+ countries. Same day: Gran Premio New York City (pro-am race, not listed).

Event siteSources: nyc.gfny.com nyc.gfny.com

The town

Once you’re in New York

SleepHotels in New York4 picks · ask about the bike when you book EatRestaurants in New York4 picks, night before and after FixBike shops in New York4 shops · 2 rent bikes

The New York town guide →

Dates

Sun, May 16, 2027 · projected

Where

Lynchburg, VA

Distances

27, 45, 49, 75 and 100 miles

Elevation

100-mile route climbs to the highest point of the Blue Ridge Parkway in Virginia

Format

Blue Ridge Parkway century (13-mile Thunder Ridge climb)

Cause

Community — YMCA of Central Virginia Community Support Campaign

Organizer

YMCA of Central Virginia

DateRide is traditionally the third Sunday of May.

NotesBenefits the YMCA incidentally; identity is the Thunder Ridge climb.

CheckNot checked with the organizer yet. Look at their site before you plan around it.

Event siteSources: strambecco.com

Dates

Sun, May 16, 2027

Where

Watsonville, CA

Distances

Road 30 mi / 100 km / 100 mi; gravel 13 / 41 / 53 mi

Elevation

872 / 3,244 / 6,041 ft (road)

Format

benefit century with gravel options (Cyclists for Cultural Exchange)

Cause

Cyclists for Cultural Exchange

Organizer

Cyclists for Cultural Exchange

Registration

Open on BikeReg; $90-$115 road, price increases 3/17, 4/17, 5/16

DateOrganizer: 36th annual ride Sunday May 16, 2027.

Event siteSources: cyclistsforculturalexchange.org

Dates

Tue, May 18 – Sat, May 22, 2027 · projected

Where

Spring Mills (Seven Mountains Scout Camp), PA

Distances

Stages: Poe Paddy 30 mi, Gettis Ridge 24 mi, Cooper's Gap 35 mi, Tussey Ridge 34 mi, Bald Eagle 21 mi

Format

5-day (or 3-day) MTB stage race

Organizer

Trans-Sylvania Productions

Lottery

No lottery.

DateDate not confirmed yet. Check the organizer’s site.

Event siteSources: strambecco.com

Dates

Thu, May 20 – Sun, May 23, 2027

Where

Asheville, NC to Greenville, SC, NC

Route

Asheville, NC → Greenville, SC

Distances

250 mi over 4 days (Blue Ridge)

Format

arthritis 4-day supported tour

Cause

Arthritis — Arthritis Foundation

Min. fundraising

$4,000

Organizer

Arthritis Foundation Cycling Experience (AFCE)

Registration

Capped at 150 riders; hotels, meals, SAG included

DateOrganizer announced May 20–23, 2027 (Bicycle Retailer, July 24, 2026).

Event siteSources: bicycleretailer.com

Dates

Thu, May 20 – Sat, May 22, 2027 · projected (2026 was May 21–23)

Where

Seven Mountains Scout Camp, Spring Mills, PA

Distances

~225 mi / 15,000 ft over 3 stages

Format

3-day gravel stage race

Organizer

Trans-Sylvania Productions

Registration

$300–500; ~200 riders.

Lottery

No lottery.

Date2026 edition May 21–23, 2026; 2027 not announced -> May 20–22, 2027 projected.

Event siteSources: gravelgodcycling.com strambecco.com

Dates

Fri, May 21 – Sun, May 23, 2027

Where

Harbor Springs to Mackinaw City, MI

Distances

51 mi (shorter options)

Elevation

rolling

Format

point-to-point party ride (Harbor Springs to Mackinaw City)

Organizer

Zoo-De-Mack Inc

Registration

2027 waitlist sign-up open (Google Form); full registration not yet open

DateOrganizer site lists May 21-23, 2027 (37th annual); ride day is Saturday May 22 with weekend events Fri-Sun.

NotesIncludes Mackinac Island ferry/party; sells out.

Event siteSources: zoo-de-mack.com

Dates

Sat, May 22, 2027

Where

Cambridge, NY

Distances

61, 45, 23, 7 miles ($80/$70/$50/$30)

Format

gravel/mixed-surface classic

Organizer

Anthem Sports

Registration

Open (BikeReg).

Lottery

No lottery.

DateRegistration opened Jun 2, 2026 (bikereg.com/battenkill).

Event siteSources: gravelcalendar.com

Dates

Sat, May 22, 2027

Where

Shelby Township (Stony Creek Metropark), MI

Distances

~6 mi paved loop around Stony Creek Lake (Eastwood Beach Shelter)

Format

suicide-prevention family ride (12th annual, short paved loop)

Cause

Mental health — Common Ground (Michigan crisis-intervention and mental-health nonprofit)

Min. fundraising

Not published yet

Organizer

Ride 2 End Suicide

Registration

2027 registration 'coming soon' (through rallybound.org).

DateOrganizer site (ride2endsuicide.com, checked Oct 1, 2026): Saturday, May 22, 2027 at 10:00 AM; the 2027 ride is the 12th annual.

NotesShort, family-friendly loop rather than a distance ride.

Event siteSources: ride2endsuicide.com

Dates

Sat, May 22, 2027

Where

Eagan (Viking Lakes), MN

Distances

Multiple route options (typically ~10–100 mi)

Format

diabetes one-day ride

Cause

Diabetes — American Diabetes Association

Min. fundraising

Fundraising minimum varies by route (check event page)

Organizer

American Diabetes Association

Registration

2027 event page live on diabetes.org

Datediabetes.org: Saturday May 22, 2027.

Event siteSources: diabetes.org

Dates

Sun, May 23, 2027

Where

Ripton, VT

Distances

100 mi / 14,500 ft

Format

100-mile / 14,500 ft climbing gravel ride

Organizer

Endurance Society

Lottery

No lottery.

Event siteSources: gravelcalendar.com gravelcalendar.com

Dates

Sun, May 23, 2027

Where

Ukiah, CA

Distances

Long/short gravel options

Format

series round

Organizer

Hopper Adventures

Series

Grasshopper Adventure Series

Registration

Per the series site: all 2027 events $155 from Oct 1 until two months before the event, then $170, then $200 day-of if spots remain; Series Pass (all five rounds) $675. Opening date not stated.

Lottery

No lottery.

DateGrasshopper Adventure Series site (checked Oct 1, 2026) lists Ukiah Mendo Gravel Epic on May 23, 2027. Series rounds King Ridge (Mar 20) and Jackson Forest (Apr 10) now have their own entries.

Event siteSources: strambecco.com grasshopperadventureseries.com

Dates

Sun, May 23, 2027 · projected

Where

Sisters (Peterson Ridge), OR

Distances

27 mi / 1,500 ft; 14 mi; 500-rider cap; $1,000 purse

Format

singletrack XC race (Oregon XC Series)

Organizer

Mudslinger Events

Series

Oregon XC Series

Lottery

No lottery.

DateDate not confirmed yet. Check the organizer’s site.

Event siteSources: strambecco.com

Dates

Sat, May 29 – Sun, May 30, 2027 · projected (2026 was May 30–31)

Where

Ventura, CA

Format

Bike MS ride (two-day)

Cause

MS — National Multiple Sclerosis Society

Min. fundraising

$350

Organizer

National MS Society

Registration

2027 TBA

Date2026 ride May 30-31, 2026 (Ventura); projected to the corresponding late-May weekend May 29-30, 2027 (Memorial Day weekend in 2027 - the organizer may shift).

Event siteSources: events.nationalmssociety.org

Dates

Sat, May 29, 2027 · projected (2026 was May 23)

Where

Rockton (Rockford), IL

Distances

32, 45, 64 mi

Elevation

rolling

Format

club invitational (Rockford area)

Organizer

Blackhawk Bicycle & Ski Club

Registration

2026: $35 before May 1, $40 online, $45 day-of

DateProjected: Saturday of Memorial Day weekend (2026 edition Saturday May 23, 2026). No 2027 date published.

NotesRockford's club invitational.

Event siteSources: bbsc.clubexpress.com

Dates

Sat, May 29, 2027 · projected (2026 was May 30)

Where

Redmond, WA

Distances

50, 70 and 100 miles

Elevation

~4,000 ft on the century

Format

century

Cause

Cascade Bicycle Club

Organizer

Cascade Bicycle Club

Registration

2027 registration not yet open as of Sept 2026

DateNo 2027 date published. 2026 was Sat May 30, 2026 (Memorial Day weekend Saturday). Memorial Day 2027 is May 31, so the corresponding Saturday is May 29, 2027.

NotesLong-running Cascade century through the Snoqualmie Valley; popular as STP training.

Event siteSources: cascade.org cascade.org

Dates

Sat, May 29, 2027

Where

Lebec / Frazier Park, CA

Distances

100 mi (the double-century format is no longer offered)

Elevation

8,750 ft

Format

mountain century in Los Padres NF; Quadzilla stage 3

Cause

Life Sports Foundation

Organizer

Planet Ultra Inc

Registration

Opens Dec 31, 2026; ~$159; 50-rider minimum; 10-hour limit

DatePlanet Ultra: May 29, 2027.

NotesSmall field (50-60 riders).

Event siteSources: planetultra.com planetultra.com

Dates

Sat, May 29 – Sun, May 30, 2027

Where

Durango (to Silverton), CO

Distances

McDonald's Citizen Tour 50 miles Durango to Silverton; Coca-Cola Road Race on the same 50-mile course; Quarter Horse 25 miles to Purgatory Resort (2,300+ ft); LaStrada LaPlata Gravel Race 55 miles; Subaru Mountain Bike Race

Elevation

Two passes above 10,000 ft (Coal Bank and Molas) on the 50-mile Durango-Silverton route

Format

multi-discipline festival weekend: citizen road tour, road race, gravel and MTB races

Cause

Iron Horse Bicycle Classic, a registered Colorado not-for-profit

Organizer

Iron Horse Bicycle Classic (nonprofit)

Registration

REGISTRATION OPENS DECEMBER 4, 2026 for the 2027 edition

DateThe official Iron Horse Bicycle Classic site carries a 'SAVE THE DATE' for Saturday May 29 and Sunday May 30 with 'REGISTRATION OPENS DECEMBER 4, 2026' - that combination identifies the 2027 (54th) edition, since the 53rd edition ran May 22-24, 2026. May 29-30, 2027 is Memorial Day weekend (Memorial Day = Mon May 31, 2027).

NotesThe famous 'Race Against the Train' - riders race the Durango & Silverton Narrow Gauge Railroad steam train to Silverton. The citizen tour (untimed) is the mass-participation event; the road race is the competitive version. Friday brings registration and the kick-off parade; Sunday has gravel/MTB racing and a cycling festival.

Event siteSources: ironhorsebicycleclassic.com cyclingwest.com

Dates

Sat, May 29 – Mon, May 31, 2027 · projected

Where

Killington, VT

Distances

Circuit race, road race and time trial; USAC categories incl. masters/juniors

Format

3-day amateur stage race

Organizer

Killington Stage Race

Registration

2027 TBA

Qualification

USA Cycling license

DateHeld every Memorial Day weekend (Sat-Mon); 2027 projected May 29-31, 2027. Organizer has not published 2027 dates.

Event site

Dates

Sat, May 29 – Sun, May 30, 2027 · projected (2026 was May 23–24)

Where

Columbia to Boonville, MO

Distances

~33 mi each way on crushed-limestone Katy Trail

Elevation

flat

Format

two-day music-festival ride on the Katy Trail

Organizer

Off Track Events

Registration

2026: $95 weekend pass, limit 1,750; youth free

DateProjected: Memorial Day weekend Sat-Sun (2026 edition May 23-24, 2026). No 2027 date published.

NotesTrail surface (not pure road).

Event siteSources: bikeiowa.com

Dates

Sat, May 29, 2027 · projected

Where

Burlington, IA

Distances

Criterium with the Snake Alley cobbled switchback climb each lap; pro-am and USAC categories

Format

criterium up the 'crookedest street' (Snake Alley)

Organizer

Snake Alley Criterium / Bike Burlington

Qualification

USA Cycling license

DateHeld every Memorial Day weekend Saturday in Burlington, IA; 2027 projected Sat May 29, 2027. Not yet announced.

Event site

Dates

Sun, May 30, 2027 · projected

Where

Bend / Sisters, OR

Distances

Big 91 mi / 8,533 ft; Medium 63 mi; Small 44 mi

Format

single-day gravel race (former stage race)

Organizer

Breakaway Promotions

Series

Oregon Gravel Grinder Series

Lottery

No lottery.

DateDate not confirmed yet. Check the organizer’s site.

Event siteSources: strambecco.com

Dates

Sun, May 30, 2027 · projected (2026 was May 24)

Where

Chippewa Falls (Eau Claire), WI

Distances

35, 50, 75, 100 mi

Elevation

rolling

Format

community century

Cause

Children

Organizer

Chippewa Valley Century Ride (non-profit)

Registration

2026: $55-$85 adult, $10 youth

DateProjected: Sunday of Memorial Day weekend (2026 edition Sunday May 24, 2026). No 2027 date published.

Notes40th anniversary in 2026.

Event siteSources: raceentry.com

Dates

Sun, May 30, 2027 · projected (2026 was May 24)

Where

Lake in the Hills, IL

Distances

Hub-and-spoke: 15 mi to hub then four loops of 13-21 mi; all four = 101 mi (25-100 mi options)

Elevation

rolling

Format

hub-and-spoke century

Cause

Environment — People for Parks Foundation of Lake in the Hills

Organizer

Race Production by Trudy (Trudy Wakeman)

Registration

2026 online registration closed

DateProjected: Sunday of Memorial Day weekend (2026 edition Sunday May 24, 2026). No 2027 date published.

NotesStart Sunset Park.

Event siteSources: raceroster.com