Located in the picturesque town of Orient, Oysterponds Shellfish Co. was founded in 2003 after an aquaculture science project grew into a thriving operation. Today, the farm produces what many consider the epitome of East End oysters, distributing nationwide while remaining committed to quality and sustainability.

Intimate summer tours are available exclusively for our guests.

Located in Mattituck on the North Fork, Macari Vineyards is a family-owned estate renowned for its commitment to organic and biodynamic farming. With sweeping views of the Long Island Sound and over 50 years of agricultural heritage, Macari has become a leader in regenerative viticulture.

Harbor Front Inn guests receive priority reservations and a complimentary sparkling wine welcome toast upon arrival. Be sure to note “Guest of The Harbor Front Inn” when booking via Tock to access these exclusive perks. If reservations are full, our team will do our best to accommodate.

As the founding vineyard on the North Fork, Borghese is rooted in tradition and a passion for producing exceptional old-world style wines. Since 1999, the Borghese family has cultivated this historic estate with care and craftsmanship, now led by second-generation owner Giovanni Borghese. Guests are encouraged to explore the scenic property, enjoy a picnic, snap a photo by the mural, or book a private tour.

Harbor Front Inn guests receive exclusive discounted access to the Founders Tour, led by Giovanni himself. This experience includes a behind-the-scenes look at the vines, private wine cellar, and barrel hall.

Rooted in a rich Mexican winemaking heritage, RGNY brings a global perspective to the North Fork. The Rivero González family blends tradition with innovation to craft expressive wines that honor their legacy while embracing a new chapter in New York.

Harbor Front Inn guests receive exclusive discounts on vineyard experiences, including tastings and events.

Set on 40 breezy acres in the North Fork, Sparkling Pointe is dedicated entirely to estate-grown sparkling wines made in the traditional Méthode Champenoise. With a focus on sustainability and classic Champagne varietals—Pinot Noir, Pinot Meunier, and Chardonnay—each bottle is a refined expression of place and craftsmanship.

Harbor Front Inn guests are invited to a Sunday Sparkling Tour & Tasting, exclusively held at 12:30 pm with 8 reserved spots each weekend. More times may be added based on demand—advance booking is recommended.

Located in Greenport, Matchbook Distilling Co. is an experimental distillery dedicated to crafting small-batch spirits that celebrate agriculture, science, and tradition. With a focus on biodiverse ingredients and flavor innovation, each release is a one-of-a-kind expression of their research-driven process.

Harbor Front Inn guests receive exclusive discounts on the following experiences:

• Whiskey Experience: “Ricks, Racks, Whisk(e)y & Thieves”
  • 20% off. Includes a welcome whiskey, distillery tour, four barrel tastings, char-level symposium, and 10% off bottle purchases.
• Bespoke Gin Session
  • 20% off. Includes spirit tasting techniques, a guided gin-blending session (750ml bottle to take home), a cocktail made with your creation, and a tour.
• “En Mid Palate” Experience
  • 10% off. Enjoy a welcome cocktail, cheese & meat board, a flight of four spirits, distillery tour, and 10% off bottles.

Tasting room open Saturdays, 1 pm to 6 pm. Reservations encouraged.

A beloved Greenport institution, Aldo’s Café offers more than just exceptional coffee—it’s a welcoming space where locals and visitors alike feel instantly at home. With its charming ambiance and strong sense of community, it captures the heart of village life, one cup at a time.

This family-owned organic farm in Southold is celebrated for its vibrant, biodynamically grown produce—especially its lettuces. With a philosophy rooted in harmony with nature, KK’s goes beyond conventional farming to nurture the land and its ecosystems.

Harbor Front Inn guests are invited to enjoy exclusive, intimate farm tours during the summer season.

VEME Studios is a welcoming creative space where artists of all kinds can explore and play across a variety of mediums. Founders Verona and Melissa offer workshops designed to engage your hands and relax your mind in a warm, inclusive environment.

Harbor Front Inn guests receive 10% off all art bar sessions and classes.

A vibrant, community-driven group supporting artists of all mediums and skill levels, NFAC fosters collaboration and creative growth on the North Fork. Their rotating exhibitions and projects bring fresh energy to the local arts scene.

Now housed in the historic Fiedler Gallery at 207 Main Street, downtown Greenport, the gallery is open Saturdays from Noon to 5 pm and by appointment other days. NFAC also curates artwork displayed and available for purchase on the first floor of The Harbor Front Inn.

Harbor Front Inn guests can enjoy exclusive access to NFAC’s curated art collection onsite. Follow @nofoartcollective on Instagram for updates.

Located in the heart of Greenport Village near the harbor, the historic Greenport Theatre serves as a vibrant cultural hub for film, live performances, art exhibitions, lectures, and hands-on arts education. As a nonprofit dedicated to enriching our community through creativity and the arts, it offers an inspiring space for all to gather and connect.

Harbor Front Inn guests receive a complimentary small popcorn with keycard presentation, plus access to discounted ticket rates using special room codes.

The only hot yoga studio on the North Fork, located just steps from Harbor Front Inn in Greenport’s Sterlington Commons. Offering classes for all levels seven days a week.

Harbor Front Inn guests receive exclusive discounts on classes.