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

Cabo Sport Fishing Adventure

6 guests
4 nights

Curacao Shores

4 guests
3 nights

La Fortuna Luxury

6 guests
7 nights

St Martin Sunsets

4 guests
5 nights

Virginia Vineyards

6 guests
3 nights

Your Cabo San Lucas experience includes 4 nights for up to 6 guests in a sleek ocean-view apartment minutes from the beach

Unwind on your private ocean-view terrace with shaded alfresco lounge. Embrace the sportfishing getaway of a lifetime with two full days of all-inclusive deep-sea fishing. Enjoy access to shared amenities including an infinity swimming pool, gym, and clubhouse. Discover downtown’s world-famous nightlife and the golden sands of Medano Beach under 10 minutes away. Benefit from Premium Guest Services for trip planning.

Bedroom 1: King size bed · Private bathroom
Bedroom 2: Olympic queen size bed · Shared bathroom
Bedroom 3: Olympic queen size bed · Shared bathroom

Winners have 12 months from the purchase date to confirm their reservation and up to 18 months from the purchase date to travel. Subject to availability and travel year-round with the exception of July 4th, Christmas, and New Year weeks. Please inquire for details. Please note, images displayed show multiple apartments. Your apartment may differ from those pictured. Bedroom configurations and bed sizes are subject to change based on group specifications. Please see your winner certificate for full terms and conditions.

Your Curaçao experience includes 3 nights for up to 4 guests in a modern beach-view apartment in a beautiful resort steps from the beach

Seek tranquility in the tropics in your modern apartment with private terrace. Soak up golden rays from the shared resort pool surrounded by gardens. Discover the charms of colorful Willemstad, just a 10-minute drive away. Wander soft sands with Blue Bay Beach on your doorstep. Embrace island activities with resort tennis, golf, water sports, and more. Sample the flavors of Curaçao with on-site dining and famed truk’i pan food trucks nearby. Benefit from Premium Guest Services for trip planning.

Bedroom 1: Queen size bed · Private bathroom · Rainfall shower · A/C
Bedroom 2: Queen size bed · Private bathroom · Rainfall shower · A/C

Winners have 12 months from the purchase date to confirm their reservation and up to 24 months from the purchase date to travel. Subject to availability and travel year-round with the exception of Christmas and New Year weeks. Please inquire for details. Please note, images displayed depict a selection of apartments; your apartment may differ from the images shown and will be allocated according to availability. No specific apartment is guaranteed. Please note, use of some resort facilities may incur additional charges. Please see your winner certificate for full terms and conditions.

Your Costa Rican experience includes 7 nights for 6 guests in a luxury villa in La Fortuna, minutes from Downtown and breathtaking natural landmarks

Refresh in the private swimming pool surrounded by tropical foliage. Sit back and relax with housekeeping services included. Sample local flavors with a welcome hamper provided upon arrival. Embrace family fun with a BBQ, pool table, ping pong, foosball, and alfresco dining. Hike the world-famous Arenal Volcano just 40 minutes away. Reach La Fortuna’s vibrant Downtown in just 10 minutes. Benefit from Premium Guest Services for trip planning.

Primary Bedroom: King size bed · Private bathroom · TV · Walk-in closet · Mini bar · A/C · Balcony access · Volcano views Bedroom 2: King size bed · Shared bathroom · TV · A/C Bedroom 3: King size bed · Shared bathroom · TV · A/C Bedroom 4: Queen size bed · Shared bathroom · TV · A/C Bedroom 5: Queen size bed · Shared bathroom · TV · A/C

Winners have 12 months from the purchase date to confirm their reservation and up to 24 months from the purchase date to travel. Subject to availability and travel Saturday to Saturday year-round. Please inquire for details. Please note, this property has a recommended occupancy of 6 adults and 4 children. Please see your winner certificate for full terms and conditions.

Your St. Martin experience includes 5 nights for up to 4 guests in an ocean view condo in Cupecoy

Experience Caribbean bliss with a 2-hour sunset cruise included. Lose yourself in 180° ocean views from two private terraces. Enjoy a lazy morning with a private in-home chef brunch included. Explore the secluded sands of Cupecoy beach just 400 meters away. Unwind at home with shared rooftop pool and housekeeping service. Benefit from Premium Guest Services for trip planning.

Bedroom 1: King size bed · En-suite bathroom · Walk-in shower · Standalone bathtub · Ocean views · Terrace access
Bedroom 2: King size bed · En-suite bathroom · Walk-in shower

Winners have 12 months from the purchase date to confirm their reservation and up to 24 months from the purchase date to travel. Subject to availability and travel between April 15th and December 17th with the exception of Thanksgiving week. Please inquire for details. Please see your winner certificate for full terms and conditions.

Your Blue Ridge Mountains experience includes 3 nights for up to 6 guests in a renovated vineyard farmhouse near Lovingston, Virginia

Sample exquisite wines on an included vineyard tour and tasting. Experience the tranquility of wine country living with ample alfresco space. Wake up to beautiful vineyard vistas with three cozy bedrooms to choose from. Savor long lunches or starlit dinners beneath the outdoor pergola. Embrace the outdoors with hiking and biking trails nearby. Discover the region’s history with Charlottesville and Lynchburg 40 minutes away. Benefit from Premium Guest Services for trip planning.

Bedroom 1: King size bed · En-suite bathroom · Walk-in shower · Standalone bathtub · Ocean views · Terrace access Bedroom 2: King size bed · En-suite bathroom · Walk-in shower

Winners have 12 months from the purchase date to confirm their reservation and up to 24 months from the purchase date to travel. Subject to availability and travel year-round with the exception of Thanksgiving, Christmas & NYE weeks, and Fridays & Saturdays during May, June, September, and October. Please inquire for details. Please see your winner certificate for full terms and conditions.