Pictures with the Grrrinch at Two Bostons

Downtown Naperville comes alive with holiday spirit every November, and this year the fun starts early with a visit from a familiar green grump. Pictures with the Grrrinch at Two Bostons invites pet owners and their four-legged family members to create memorable holiday photos right in the heart of downtown.

Whether you’re a longtime Naperville resident or visiting for the weekend, this pet-friendly gathering at the popular local boutique on West Jefferson Avenue gives you a chance to capture the season’s playful side without any fuss.

Why You Can't Miss Pictures with the Grrrinch at Two Bostons

The Grrrinch returns to Two Bostons for another round of holiday mischief, ready to pose with your pets in a setting that feels perfectly at home in downtown Naperville. This event continues the store’s tradition of welcoming the community’s furry friends for seasonal photo opportunities that everyone enjoys.

One of the Best Free Things to Do in Naperville This Weekend

Mark your calendar for Saturday, November 7, 2026, between 11:00 AM and 1:00 PM at Two Bostons, 103 W. Jefferson Avenue. Bring your leashed pet for a quick photo session snapped right on your own phone…no waiting for prints or professional setups required. Grumpy expressions are not only allowed but encouraged for that authentic Grrrinch vibe.

After the photo, your pet can create a festive paw print painting to take home as a keepsake. Multiple pets are welcome as long as they remain safely leashed. The relaxed, drop-in format makes it easy to stop by while exploring downtown Naperville’s shops and nearby Riverwalk.

What to Expect at the Event

Two Bostons staff will guide you through the simple process so you leave with shareable photos instantly. The boutique’s welcoming atmosphere and pet-friendly reputation make this a comfortable stop for dogs of all sizes and temperaments.

• Phone photos taken on-site for immediate sharing
• Paw print painting activity for a take-home memento
• No registration or tickets needed…just drop in during the two-hour window

Plan Your Visit

Two Bostons sits in the center of downtown Naperville, making it simple to combine with a stroll along the Riverwalk or a visit to nearby landmarks like Naper Settlement. Street parking and public lots are available in the area, and the event runs for a convenient two-hour window that fits easily into weekend plans.

• Arrive early if you have multiple pets or want to avoid any wait
• Leashes and good behavior are expected for everyone’s comfort
• After your visit, explore Century Walk sculptures or grab a bite nearby

Stop by Two Bostons on November 7 for a lighthearted start to the holiday season with your pet. It’s the kind of simple, local tradition that makes Naperville feel like home.

Event Details At-A-Glance

• When: Saturday, November 7, 2026, 11:00 AM…1:00 PM
• Where: Two Bostons
• Address: 103 W. Jefferson Avenue, Naperville, IL 60540, United States
• Organizer: Two Bostons
• Tickets / info: Get details

Dates, times, and pricing can change. Confirm the latest details on the official event page before making plans.

Looking for more? Explore other things to do in Naperville or browse the full Naperville events calendar.