Harbor Point Vacation Rentals

Trivia Tuesdays at Crooked River Grill
2026-05-12 18:00 - 19:30, 2026-05-19 18:00 - 19:30 (America/New_York) | Crooked River Grill, 133 Quail Ln, Monticello, FL, United States
Get ready for the most entertaining night of the week at Crooked River Grill! Join us every Tuesday from 6–7:30 PM for Trivia Night hosted by the one and only Cecily Stevens—bringing the energy, the laughs, and just the right amount of competitive chaos.
Expect plenty of hootin’ and hollerin’, fast-paced fun, and questions that’ll keep your brain firing on all cylinders. Whether you’re a trivia junkie or just here for a good time, this is your chance to test your knowledge, rally your crew, and maybe even walk away with bragging rights.
Even better? It’s all for a great cause. Entry is just $2, and every dollar goes toward supporting a different local nonprofit each month—so you can feel good while you’re having a blast.
Come soak in the atmosphere, enjoy the beauty of the property, and bring your A-game.
You bring the brains—we’ll bring the teasers.

Creation Station: Sand Art Jars
2026-05-13 16:00 | Eastpoint Public Library, 159 Hickory Dip Rd, Eastpoint, FL, United States
Creation Station: Sand Art Jars, a program where children ages 7–12 can mix and match colors to make a sand art jar to take home. The program will be held on Wednesday, May 13 at 4:00 PM at the Eastpoint Branch.

Adult Crafternoon: Oyster Flowers
2026-05-14 14:30 | Eastpoint Public Library, 159 Hickory Dip Rd, Eastpoint, FL, United States
Adult Crafternoon: Oyster Flowers will take place on Thursday, May 14 at 2:30 PM at the Eastpoint Branch. Adults can learn how to make an Oyster Flower! This easy hands-on program will be provided in a relaxed, welcoming setting and is open to adults of all skill levels.

Yappy Hour at the Beer Garden
2026-05-14 15:00 - 18:00, 2026-05-21 15:00 - 18:00 | Crooked River Grill, 133 Quail Ln, Monticello, FL, United States
Thursdays just got a whole lot better, for you and your pup. Yappy Hour at St. James Bay is the perfect excuse to kick back in our laid-back outdoor setting, where the breeze off the bay, warm sunshine, and easygoing vibe set the tone for a relaxing afternoon.
While you enjoy happy hour food and drink specials, your dog gets the VIP treatment with free snacks and fresh water bowls, because they deserve a good time too. It’s part social hour, part puppy party, with plenty of tail wags, cold drinks, and great company all around.
Grab a seat, bring your pup, and settle in. This is what afternoons at the bay are all about.

Video Game Hour
2026-05-15 16:30 | Carrabelle Library, 311 St James Ave, Carrabelle, FL, United States
The Friends of the Franklin County Public Libraries (FFCPL) are pleased to announce that the popular Video Games Hours for teens and tweens continues this March at the Carrabelle Branch Library. These sessions are part of the Program Series, offering something for everyone – young children, students, and lifelong learners. These events are open to the public—no library card is required—and offer a welcoming, inclusive space for individuals of all ages to learn, explore, and connect through technology.
Video Game Hour will be held on Friday, May 1 at 4:30 pm at the Carrabelle Branch. Teens and tweens are invited to unwind and compete on the Nintendo Switch during these fun and casual gaming hours.
Another Video Game Hour will be held on Friday, May 8 and May 15 at 4:30 pm at the Carrabelle Branch. Teens and tweens are invited to unwind and compete on the Nintendo Switch during these fun and casual gaming hours.

Live Music in May at Crooked River Grill
2026-05-15 18:00 - 21:00 | Crooked River Grill, 133 Quail Ln, Monticello, FL, United States
We’re excited to feature Jon White
Nothing pairs better than great food, coastal views, and live music.
Come join us at Crooked River Grill for relaxing evenings filled with local talent and good vibes on the patio.

Country Farmer’s Market in Carrabelle
2026-05-16 09:00 - 13:00 | Crooked River Lighthouse, 2100 Hwy 98, Carrabelle, FL, United States
The Crooked River Lighthouse continues to host its popular Country Farmers Markets on the 1st and 3rd Saturdays of each month from 9 am to 1 pm ET at the foot of Carrabelle’s historic lighthouse. These lively markets are the perfect chance to shop small, shop local, and discover unique gifts and tasty treats while supporting regional vendors, artists, bakers, artisans, and crafters. The lighthouse is located at 1975 Hwy 98 West, Carrabelle, FL.
Market-goers will find a wide selection of offerings, including organic farm-fresh produce, grass-fed beef, fresh eggs, aromatic herbs, artisan breads and baked goods, mouthwatering cinnamon rolls, batch-roasted coffee, assorted jellies, homemade hot sauces and salsas, handcrafted balms and sprays, locally made jewelry, stunning art and décor, unique clothing and t-shirts, plants and other handmade goods and craft items. Throughout the year, the market also features special activities like book signings, live music, children’s activities, paint parties, and photography classes, adding to the fun and community spirit.
Visitors are encouraged to extend their visit by exploring the free Keeper’s House Museum, which houses the historic Fresnel lens, and by browsing the lighthouse gift shop, open from 9 am to 5 pm ET. The shop offers an array of handcrafted items, jewelry, coastal art, nautical décor, souvenirs, and keepsakes. For those seeking a little extra adventure, a climb to the top of the lighthouse rewards guests with a breathtaking panoramic view of St. George Sound (small fee applies).
New and returning vendors are welcome to join any time for $10 per market by emailing carrabellelighthouse@gmail.com. For more information, call 850-697-2732 or visit www.crookedriverlighthouse.com. Funded in part by the Franklin County Tourist Development Council.

Live Music in May at Crooked River Grill
2026-05-16 17:00 - 21:00 | Crooked River Grill, 133 Quail Ln, Monticello, FL, United States
We’re excited to feature Evan Barber
Nothing pairs better than great food, coastal views, and live music. Come join us at Crooked River Grill for relaxing evenings filled with local talent and good vibes on the patio.
Bring your friends, enjoy your favorite drinks, and let the music set the tone for a perfect night out. 🍹🎸

Pool Party at St James Bay
2026-05-18 12:00 - 16:00 | St. James Bay Golf and Pickleball Resort, 151 Gayla Ct, Portland, TN, United States
Come join us for a fun filled pool party at St. James Bay Golf & Pickleball Resort!
We’ll have DJ Tiggs spinning great music from 12-4pm, plus delicious food and drink specials to keep the party going.
Bring your friends, soak up the sun, and enjoy a day of great vibes, good company, and poolside fun.
Hope to see you there!

Yoga @ Apalachicola Library
2026-05-18 18:00 - 19:00 | Apalachicola Margaret Key Library, Apalachicola, FL, United States
Yoga class led by Kathy Jansen (CYT 200 & 500) with Spirit of the River Yoga Studio and Store (https://www.spiritoftheriveryoga.com/) . Class is by-donation, and begins shortly after 6pm when the library closes for business. Come early to sign a liability waiver, set out your mat and get comfortable. Some mats/blocks/straps/blankets available for use, though attendees are encouraged to bring their own.

Apalach Ghost Tour
2026-05-18 20:00 - 21:30 | Apalachicola
Join us for local ghost stories, area legends, and tales of hauntings in downtown Apalachicola while using ghost-hunting equipment to seek out any lingering spirits. Select tour goers and volunteers will get to use EMF detectors, and other ghost-hunting equipment at select locations on the tour. Bring your positive energy and let’s try to say “hello” to the ghosts of Apalachicola. The tour will begin in front of the Chamber of Commerce which is located at 17 Avenue E next to the Dixie Theatre. This tour ranges in length from an hour and a half to an hour and 45 minutes.

Live Music in May at Crooked River Grill
2026-05-22 17:00 - 21:00 | Crooked River Grill, 133 Quail Ln, Monticello, FL, United States
We’re excited to feature Noah Swanson
Nothing pairs better than great food, coastal views, and live music. Come join us at Crooked River Grill for relaxing evenings filled with local talent and good vibes on the patio.
Bring your friends, enjoy your favorite drinks, and let the music set the tone for a perfect night out. 🍹🎸

Pickleball Tournament
2026-05-23 08:00 - 2026-05-24 17:00 | St. James Bay Golf and Pickleball Resort, 151 Gayla Ct, Portland, TN, United States
St James Bay Golf and Pickleball Resort is hosting a Pickleball Tournament event date May 23 & 24, 2026. Early registration price $40 before May 11, 2026 $60 after, includes tournament, meet and greet, lunch, and more. it’s a party at the bay come join us! Need a place to stay we have lodging call us to book a room 850-697-9606. Crooked River Gill is open from 8am-9pm Monday – Sunday

Apalachicola Farmers Market
2026-05-23 09:00 - 13:00 | 133 Avenue E, 133 Avenue E, Apalachicola, FL, United States
Located at 133 Avenue E, across from CVS, the Apalachicola Farmers Market offers local seafood, produce, honey, homemade breads, pies, and other regional specialties every 2nd and 4th Saturday from 9 AM until 1 PM in Apalachicola.

Live Music in May at Crooked River Grill
2026-05-23 17:00 - 21:00 | Crooked River Grill, 133 Quail Ln, Monticello, FL, United States
We’re excited to feature David McMahon
Nothing pairs better than great food, coastal views, and live music. Come join us at Crooked River Grill for relaxing evenings filled with local talent and good vibes on the patio.
Bring your friends, enjoy your favorite drinks, and let the music set the tone for a perfect night out. 🍹🎸

Apalachicola Memorial Day Celebration – Veterans Memorial Plaza
2026-05-25 10:00 - 11:30 | Apalachicola Veterans Plaza, 230 Market St, Apalachicola, 32320
Join us and our iconic Three Soldiers Statue at our Veterans Memorial Plaza on 230 Market street for a special annual event. You do not want to miss the celebration as we remember and honor our local heroes who made the ultimate sacrifice. Visit our website to see gallery of past events.
Memorial Day… Gather, Remember and Honor
