Carriage Rides
2025-11-29 16:00 - 20:00, 2025-12-05 16:00 - 20:00, 2025-12-06 16:00 - 20:00, 2025-12-12 16:00 - 20:00, 2025-12-13 16:00 - 20:00, 2025-12-19 16:00 - 20:00, 2025-12-20 16:00 - 20:00, 2025-12-26 16:00 - 20:00 (America/Kentucky/Louisville) and 1 more date | Downtown Pikeville, Pikeville, Ky, 41501
We are pleased to announce that carriage rides will be offered this Friday and Saturday from 4-8.Guests can enjoy a relaxing, scenic ride for $15 per person.This is a wonderful opportunity for families, couples, and individuals to experience a charming and traditional carriage outing.We look forward to providing you with a memorable and enjoyable experience.Call and book with us at 606-794-9881

Sit N Sew Beginners
2025-12-04 17:00 - 21:00, 2025-12-11 17:00 - 21:00, 2025-12-18 17:00 - 21:00, 2026-01-08 17:00 - 21:00, 2026-01-15 17:00 - 21:00, 2026-01-22 17:00 - 21:00, 2026-01-29 17:00 - 21:00, 2026-02-12 17:00 - 21:00 and 6 more dates | Bridgett’s Quilting and Fabric Shop, 237 2nd St,, Pikeville, KY, 41501, United States
Come and Join Us

Merry on Main
2025-12-06 17:00 - 21:00 | Downtown Pikeville, Pikeville, Ky, 41501
Who is READY to Sip, Shop & Save Downtown?Go ahead and tag your shopping buddies, friends and family!The first 100 guest to visit The Shoppes at 225 on Saturday may purchase a Red Bag with exclusive coupons, $10 Downtown Dollars and more!Join us for a MeRrY mix of savings and seasonal cheer—your perfect excuse to shop local and celebrate! Date: Saturday, December 6 Location: Downtown Pikeville Tag your shopping squad and make it a holiday to remember!

Free Christmas Wrapping
2025-12-20 11:00 - 15:00 | The Shoppes at 225, 225 2nd St, KY, 41501, United States
Who needs a little help getting their Christmas Presents wrapped this Christmas? WE Got You!Let our volunteers Take the STRESS out of your holiday season—bring your gifts and enjoy **complimentary gift wrapping** by our amazing volunteers. All we ask is that you **TIP the organization WRAPPING for YOU**—your generosity helps support their incredible work!

Tax Credit Program
2026-03-05 18:00 - 19:00 | Online Event, Pikeville, KY, 41501, United States
Attention Downtown Property Owners!

We wanted to share an important opportunity coming up. The Kentucky Heritage Council (KHC) is hosting a FREE, virtual webinar about Kentucky’s Historic Rehabilitation TAX Credit Program on Thursday, March 5, 2026, from 6:00–7:00 PM ET. It’s designed especially for those who OWN property in the Downtown Historic District.

This session is open to the public for FREE and will give an easy-to-understand overview of how historic tax credits work, who qualifies, and how these incentives can support rehabilitation and preservation projects. If you’ve ever considered improvements to your historic property, this webinar could be incredibly valuable!

Date: March 5
Time: 6:00–7:00 PM
Format: Online Webinar

You may register for this webinar at:
https://bit.ly/3ZnrbsK

PLEASE help spread the word and share with other property owners who may benefit.

Let’s continue investing in the future—and history—of our downtown!

St. Paddy's Day 5K Run/Walk
2026-03-14 15:00 - 17:00 | Downtown Pikeville, Pikeville, Ky, 41501
Wear your green to celebrate St. Patrick’s Day in Downtown Pikeville!Start your afternoon with some exercise and finish with some celebrating in our wonderful downtown district.Many thanks to Pikeville Main Street Inc for sponsoring the race! Follow us on Facebook!Race Highlights
Chip timed 5K Run/Walk
Untimed Fun Walk (about 1 mile)
Finisher Medal for all!
Overall & Age Group AwardsTop 1 Male & Female OverallTop 1 Male & Female in these age groups:10 & Under, 11-15, 16-19, 20-29, 30-39, 40-49, 50-59, 60-69, 70 & Over
Costume ContestBest Overall St. Patrick’s Day CostumeFor the participant who goes all‑in — think full leprechaun suits, gold‑themed outfits, green wigs, and shamrock accessories.Most CreativeFor the unique and unexpected — rainbows, pots of gold, Leprechauns, Lucky Fairy & Celtic SpriteBest Kids’ Costume: (10 years & Under)Cute mini‑leprechauns, fairy wings, green tutus, etc.
Costume Contest Winners announced with Overall & Age Group Awards

Downtown Pikeville Pub Crawl
2026-03-14 17:00 - 22:00 | Downtown Pikeville, Pikeville, Ky, 41501
Downtown Pikeville Pub Crawl – Presale Starts Monday!

Get ready to hit the town, Pikeville! The Downtown Pikeville Pub Crawl is coming soon, and presale tickets drop Monday, March 2!
Presale Price: $30
Day‑of Event Price: $40

Don’t wait—grab your presale ticket and save $10 while securing your spot for a night of great drinks, great friends, and great vibes in Downtown Pikeville!
Mark your calendars and call or stop by the City of Pikeville Tourism Office to get your PRESale Tickets!

Free Virtual Workshops
2026-03-25 12:00 - 13:00 | Online Event, Pikeville, KY, 41501, United States
Business owners, mark your calendars!

The first in a series of free virtual workshops is coming up soon! “The Digital Tune-up: Prepping Your Business for Online Growth” will be hosted on Thursday, March 25, from 12 – 1 p.m. ET.

In the workshop, experts from Main Street America’s Small Business Hub will walk through an essential checklist designed to catch the critical details that often slip through the cracks. We know that when you are focused on the day-to-day reality of running a business, it is easy to forget the ‘digital housekeeping’, but those small gaps can add up to big missed opportunities.

Register here: https://savingplaces-org.zoom.us/…/WN…

(Even if you can’t attend live, make sure to register! You’ll get a recorded version after the fact.)

Pictures with Sassy The Bunny
2026-04-03 17:00 - 19:00 | Pikeville City Park, 101 Cumberland Ct,, Pikeville, KY, 41501
Get ready to giggle, Pikeville! He’s fluffy, he’s photogenic, and yes, he’s got a little bit of attitude!Grab the kids, your friends, and even your pets, and come get SASSSY with the coolest bunny around. You won’t want to miss this free unique photo op with the big chair! WHEN: Friday, April 3, 2026 from 5pm – 7pm WHERE: Pikeville City ParkStrike a pose and let’s see your best “sassy” face! See you at the park!
