Lee Sportsmen's Association

10th Annual Youth Sports Gala

Saturday, May 9, 2026
101 Restaurant & Bar
at the Holiday Inn

(1 West Street, Pittsfield)

Dinner Raffles Live & Silent Auctions

Doors Open at 4pm, Dinner Served At 6pm, $125 Per Person

All-Inclusive
Tropical Resorts

2 guests
4 nights

Finger Lakes

2 guests
3 nights

Costa Rica Getaway

8 guests
6 nights

Waterfront Belize

8 guests
7 nights

Kentucky
Bourbon Trail

2 guests
2 nights

Glamping Near
the Mountains

2 guests
3 nights

Ultimate Nascar

2 guests
2 nights

5 days and 4 nights in a studio room at one of the following sample resorts: Dreams Vallarta, Dreams Cabo, Dreams Riviera Maya, Dreams Cancun, Dreams Huatulco, Secrets Vallarta, Secrets Cozumel, Sunscape Puerto Vallarta, Sunscape Cozumel, Sunscape Ixtapa, Hyatt Ziva Riviera, Hyatt Zilara Riviera Maya or Hyatt Vivid Grand Island Cancun

(Complete hotel list available upon request)

  • All meals, snacks and beverages, including alcohol

  • Non-motorized activities

  • Gratuities and hotel taxes

 

The breathtaking beaches, vibrant culture and essence of Mexico beckon you to visit and unwind, from the pristine Pacific coastline to the laid back vibes of Tulum; whether you dive into stunning waters or explore Mexican culture on dry land, you’ll be with your loved one amid the natural wonders, scenic ancient ruins, soaring cliffs, charming society, inspired art, superb food, tangy tequila, and parties along the playas in Mexico! Just a few hours south of Miami is the Dominican Republic, the second largest Caribbean country, known for its hospitality and diversity; this lush tropical island paradise boasts nearly 1,000 miles of coastline, 250 miles of the world’s top beaches, pulsing merengue music, and ancient relics! Regardless of the destination you choose, you’ll stay at a World of Hyatt Inclusive Collection resort, each one designed for you in one of nearly a dozen cherished destinations.

Package for couples only. Two or more couples are not permitted to travel together. Travel package is non-refundable and subject to availability. Certificates/gift cards cannot be replaced. Travelers must be residents of either the United States or Canada. Passport required for travel outside the U.S. Participating properties are subject to change. Travel is valid for 18 months from the date of issue. Holiday travel dates may be available at an additional cost. Any upgrades, additional nights, or adding additional guests must be booked directly with the resort after the original package booking is completed. A minimum 60 day advance reservation is required.

CANCELLATION POLICY: Cancelation more than 16 days prior to arrival is subject to rebooking with full credit. Cancelation less than 16 days prior to arrival is subject to a 2- night penalty.

It’s time to explore the Craft Beverage trails of New York States Finger Lakes region! And there’s no better place to call home during your adventure than the Black Sheep Inn and Spa in Hammondsport, NY.

With hundreds of wineries, breweries, and distilleries within an hour’s drive of the Inn, your group is sure to find some new favorites along the way.

Your trip to the Finger Lakes is highlighted by a two night stay in one of their queen rooms, a historic, boutique Bed and Breakfast Inn. Your comfortable room features distinctive décor, private en suite bathroom, plush robes, and, of course, locally sourced Farm to Table breakfast each morning. The Inn also offers several spacious common areas, both indoors and out, that provide you with the opportunity to relax with a good book, connect to their complimentary Wi-Fi, or just be in the moment to take in the fresh air, light breeze or subtle smoke from the courtyard fire pit.

  • 4 days, 3 nights accommodations at the Black Sheep Inn and Spa in a queen-bedded room

  • Complimentary tastings at five award winning partner producers around Keuka Lake

  • 4-hour guided Luxury Excursion to all partner producers

  • Inn Harvest Cooler, filled with local veggies, crackers, dips and sweet treats to keep you sated on your Craft Beverage tour

  • Two signature stainless steel insulated bottles to keep you hydrated

  • Black Sheep Guild cards valid at Guild partners for specials and perks for guests of the Black Sheep Inn and Spa

  • Special gift from the Black Sheep Inn

  • Expert travel and concierge services

  • All taxes and service charges

Travel package is non-refundable and subject to availability. Certificates/gift cards cannot be replaced. Tour runs on specific days of the week and at specific times. If tour is not available, it may be substituted with equal or similar experience. A 45-day advance reservation is required. Travel is valid for 18 months from date of issue.

Spend 6 full days and 6 nights in one of our Villas, great for 4 couples or large families. A true native experience with American luxury. Our villas are located in the beautiful country of Costa Rica and they are among the finest the country has to offer.

Located in the Playa Herradura and Playa Hermossa areas, our villas offer breathtaking views of both the mountains and the Pacific Ocean. Located minutes from the small surf villages of Jaco and Hermossa, you will enjoy a rich Central American culture with great night life as well as numerous activities on both the water and land. Spend the day doing a canopy tour over the jungle or strap in and rappel down one of the many beautiful waterfalls just minutes from your house. Costa Rica also offers world-class offshore fishing and our fleet of custom maverick sport fishing yachts can provide you with a once in a lifetime experience. Spend the day fishing and bring home your catch for one of our chefs to prepare for dinner. This is truly an exclusive and unique vacation experience in Costa Rica with true native feel while maintaining American luxury standards!

 

Transfers to and from the airport, maid service, and chef service can all be arranged for your trip at an additional rate. Golfing, fishing, waterfall rappelling, ATV tours, horseback riding, surfing lessons, canopy zip line tours are available but must be booked separately and are not a part of this package. Grocery shopping prior to arrival available.

  • 7 days, 6 nights accommodations for 4 couples or a large family at one of our Costa Rican Villas

  • $250 villa utility usage allowance

  • All villa-related taxes

  • Free concierge reservation service

  • Consignment Cost $4,995

Travel package is non-refundable and subject to availability. Certificates/gift cards cannot be replaced. Passport required for travel outside the U.S. Villa will accommodate up to 8 guests. Check in must occur on Saturday and check out must occur on Friday. A security deposit will be required at the time of booking and returned at the end of the stay. In-country service fee of $65 per person not included. Blackout dates are last 2 weeks of December including Christmas and New Year’s weeks A minimum 90 day advance reservation is required. Travel is valid for 18 months from date of issue.

CANCELLATION POLICY: Cancellation less than 120 days prior to arrival will be subject to forfeiture of reservations and funds.

The Waterfront at Your Back Door in Placencia, Belize. Set between the shorelines of the Caribbean Sea to the east, and the dense jungle to the west, the small country of Belize is a tropical gem, featuring miles of gorgeous coastline, white-sand beaches, swaying palm trees, ancient ruins, wildlife, and invigorating experiences. 

Only in Belize can you find the perfect blend of Caribbean and Central American cultures, and take advantage of the incredible geographic diversity – mountains in the morning and the shores at sunset! Invite your closest family and friends to join you on this exclusive and unique vacation to this laid-back locale for an authentic taste of the tropics, fascinating history and exhilarating outdoor adventures!

  • 8 days, 7 nights accommodations in a four-bedroom villa

  • Daily maid service

  • On-site laundry services

  • 24-hour house caretaker

  • Personal chef for three days, guests are responsible for cost of food prepared

  • Use of kayaks and paddle boards provided at villa

  • Golf cart to explore the area

  • Round trip transfers from Placencia Airport to villa

  • Free WiFi

  • On-site concierge services

  • Free concierge reservation service

Travel package is non-refundable and subject to availability. Certificates/gift cards cannot be replaced. Passport required for travel outside the U.S. A minimum 90 day advance reservation is required. Check-in and check-out must occur on Saturday. Blackout dates are Thanksgiving week and the last 2 weeks of December including Christmas and New Years. Gas coverage for golf cart not included. Limited availability January through April. Round trip transfers from Placencia Airport to villa. Travel is valid for 18 months from date of issue.

The Omni Louisville Hotel is within walking distance of top downtown attractions such as the Louisville Slugger Museum & Factory and the Mohammed Ali Center. The hotel is just a short ride away from the Kentucky Derby museum and Churchill Downs. The highlight of the trip is a personalized eight hour tour of the Kentucky Bourbon Trail in a chaufffered luxury sedan.

Whether you are first time Bourbon tasters or veteran Bourbon drinkers, you’ll enjoy an enlightening fun-filled day in the beautiful countryside of Kentucky. The informative Bourbon Trail Tour will be customized based on your individual Bourbon preferences. You will visit Distilleries such as Maker’s Mark, Jim Beam, and Wild Turkey. And you will enjoy lunch in the world famous Bluegrass countryside outside of Louisville.

  • 3 days, 2 nights accommodations at The Omni Louisville Hotel in a king or queen-bedded room

  • All room-related taxes

  • Private 8-hour Distillery tour in a chauffeured luxury sedan

  • Free concierge reservation service

Travel package is non-refundable and subject to availability. Certificates/gift cards cannot be replaced. Tour runs on specific days of the week and at specific times. If tour is not available, it may be substituted with equal or similar experience. A minimum 45 day advance reservation is required. Travel is valid for 18 months from date of issue.

Unforgettable Glamping Near the Mountains in Maine or Tennessee. Find magic under the stars with Under Canvas, which brings the beauty of nature, the iconic rocky Maine coastline in Acadia, the ever-present morning fog of Appalachia’s Great Smoky Mountains and the luxury of an elevated glamping experience together.

After spending the day exploring outdoors, return to your safari-inspired tent and relax in comfort and style, before waking up to the sights, sounds and smells of nature the following day. Under Canvas’ award-winning camps boast elevated glamping experiences in incredible locations, exceptional views, a host of activities, and of course, extraordinary natural wonders right outside your tent for a superb glamping and outdoor adventure!

At Under Canvas, the adventures don’t stop when the sun sets. In fact, with some of the darkest and clearest night skies in the world, Under Canvas camps come alive when the sun goes down—when millions of stars, star clusters, and constellations provide a once-in-a-lifetime celestial experience that you’ll treasure for years to come. Under Canvas offers unique activities and amenities that celebrate the beauty and wonder of the night sky. From complimentary stargazing and full moon hikes, to celestial-themed cocktails and unlimited s’mores, to sleeping under the stars in a Stargazer Tent, the camps offer a galaxy of unforgettable nighttime experiences.

  • 4 days, 3 nights accommodations at Under Canvas Acadia or Great Smoky Mountains

  • All room-related taxes

  • Free concierge reservation service

Travel package is non-refundable and subject to availability.

Certificates/gift cards cannot be replaced. Under Canvas Acadia operates seasonally and accepts reservations from May through October. Under Canvas Great Smoky Mountains operates seasonally and accepts reservations from April through December. Operating dates may change annually. Travel is valid for 18 months from date of issue. A minimum 90 day advance reservation is required.

Charlotte’s NASCAR roots (80 percent of Sprint Cup drivers call it home) make it the perfect city for the ultimate NASCAR experience! The Ultimate Fan Experience provides a unique insiders’ look at the sport of NASCAR for a full day, including a visit to the NASCAR Hall of Fame®. Your NASCAR adventure builds up to the most thrilling experience of all – you’ll get to drive a NASCAR-style stock car around the Charlotte Motor Speedway for eight laps!

Charlotte’s a vibrant city that combines the best of the new with good old Southern hospitality. Named in honor of English royalty, the Queen City welcomes visitors with an impressive skyline, museums, performing arts and professional sports. It’s a city that captivates both NASCAR heroes and finance leaders, and a city where Northern newcomers exchange smiles on the street with Carolina natives. Charlotte’s prime location for comfort and accessibility is in the heart of uptown near the best attractions, including the NASCAR Hall of Fame, Bank of America Corporate Center (home of the Carolina Panthers), Billy Graham Library, Uptown City Center, excellent dining options and shopping! Feel the charm of the city during your stay at the thoughtfully designed Fairfield Inn & Suites Charlotte Uptown.
  • 3 days, 2 nights accommodations at the Fairfield Inn & Suites Charlotte Uptown

  • Daily complimentary breakfast buffet

  • All room-related taxes

  • Complimentary internet service

  • Entrance to NASCAR Hall of Fame®

  • 1 Richard Petty rookie driving experience at Charlotte Motor Speedway (per person)

  • Driver release fee

  • Free concierge reservation service

Travel package is non-refundable and subject to availability. Certificates/gift cards cannot be replaced. Reservations must be made at least 60 days in advance of travel. Travel is valid for 24 months from date of issue.