There’s something special about a winter engagement session in New York. The snow, the bustling streets, the twinkle of holiday lights—it all sets the scene for photos that feel cozy, romantic, and effortlessly timeless. As a Westchester native and seasoned wedding photographer, I have had the privilege of photographing countless sessions in the city and surrounding areas. Here’s what I’ve learned when planning your session to ensure it is comfortable, fun, and memorable.

Iconic NYC Backdrops: Central Park and Pier 1

Central Park is a classic choice for winter engagement sessions. Its bridges, pathways, and open fields look stunning when dusted with snow. Additionally, Pier 1, off Riverside Blvd on the West Side, offers incredible city views, particularly at sunset, when the light reflects off the glass buildings of Manhattan.

Keep in mind, Pier 1 can feel very cold on windy days. Hand warmers, layers, and a thick coat are essential. Comfortable shoes for walking between locations make a big difference, and you can always swap into dressier shoes.

Festive Winter Streets and Holiday Lights

Winter is a great time to incorporate holiday lights into your engagement session. Walking through your hometown or city streets decorated with lights adds natural charm and warmth to your photos. These cozy, candid moments often feel playful and romantic, think Hallmark movie vibes. It’s an easy way to capture your authentic connection without overly posed shots.

For couples planning this type of session, I would typically keep the walking route relatively short—3 to 4 blocks is usually ideal. Bring hand warmers in pockets or gloves and scarfs to stay extra comfortable and present in the moment. If you are walking on a street with your favorite bar or restaurant, you could pop-in for a drink, for a fun photo opp and to warm up!

Untermyer Gardens: Light Shows and Seasonal Beauty

Untermyer Gardens in Yonkers hosts the Grand Holiday Illumination every December through early January. The illuminated gardens, combined with winter foliage and classical architecture, make for a unique and festive engagement session. Evening sessions here feel intimate and magical, and the lights add a beautiful glow to your photos without additional props.

Parks and Preserves with Evergreen Backdrops

For natural winter photos, open fields with evergreen trees are perfect. Evergreens hold their greenery even under snow, creating contrast and texture in your images. Harts Brook Park and Preserve is ideal during golden hour, with soft light filtering through the trees.

When scouting Westchester parks, look for locations with a mix of open fields and pockets of greenery. This adds visual interest and provides natural shelter from the wind while shooting.

Tips for Staying Warm During Winter Engagement Sessions

Winter sessions are beautiful, but the cold can be challenging. Here are my top tips for keeping comfortable:

1. Layer Up: Wear quality wool or thermal layers under stylish outerwear. Also, consider a neutral scarf, a thick coat, or blanket between shots helps maintain comfort.
2. Hand and Foot Warmers: Keep them in pockets, gloves, or boots for maximum warmth.
3. Warm Beverages: Coffee, tea, or hot chocolate can help you stay warm while walking between locations.
4. Timing: Schedule sessions for late morning or early afternoon when temperatures are slightly higher. Keep the session under 90 minutes in extreme cold or take breaks indoors between locations.
5. Footwear: Wear comfortable boots for walking, then swap to dressier shoes or boots for photos.

Choosing the Right Winter Engagement Locations

Here’s a quick roundup of favorite winter engagement session locations:

• Central Park: Bridges, pathways, and Bow Bridge for classic New York charm.
• Pier 1, NYC: Sunset reflections and city skyline views.
• Untermyer Gardens, Yonkers: Seasonal light shows for festive charm.
• Harts Brook Park and Preserve: Evergreen backdrops during golden hour.
• Evergreen-heavy Westchester parks: Natural greenery that stands out against snow.

Pro tip: Avoid rooftops in winter when possible. While they offer scenic city views, they are often too cold and windy for a comfortable session.

Making Your Winter Engagement Session Memorable

Your winter engagement session, specifically in New York, is all about balancing beautiful scenery with personal connection. Choosing locations that reflect your personality and story makes your photos feel authentic and timeless. Whether you’re walking through festive streets, posing beneath holiday lights, or surrounded by evergreens in a Westchester park, thoughtful planning ensures your session is comfortable, relaxed, and full of genuine moments.

With proper preparation, you can enjoy a session that captures your love story in the magic of winter. Looking for a seasoned wedding photographer to help you plan your winter engagement? I’d love to chat to see if we would be a great fit!