Glastonbury Holiday Events

Holiday House Tours on Main 2025

1944 Main Street, POBox 46, Glastonbury, CT, United States, Connecticut 06033 6 Dec 2025

Gingerbread Workshop

2450 Main Street, Glastonbury, CT, United States, Connecticut 06033 14 Dec 2025

Cookies and Playtime with Santa

2450 Main Street, Glastonbury, CT, United States, Connecticut 06033 21 Dec 2025

🎾 Black Friday Tennis & Pickleball Clinics 🏓

228 Oak St, Glastonbury, CT, United States, Connecticut 06033 28 Nov 2025

Oakwood Holiday Cup

40 Oakwood Dr, Glastonbury, CT, United States, Connecticut 06033 20 Dec 2025

Holiday Bingo Night

2941 Main St, Glastonbury, CT 06033 4 Dec 2025

Special Tasting Event - Wines from California & Italy

The Best Wine Shop in Town 3 Dec 2025

GHREI Holiday Party + Celebrating Steph!

Square Peg Pizzeria Glastonbury 9 Dec 2025

Gingerbread House Decorating Party

Chick-fil-A 16 Dec 2025

Santa's 3.5 Mile Run

Glastonbury High School 7 Dec 2025

Gingerbread House Decorating Class

Crystal Ridge Winery 4 Dec 2025

Holidays at mission

80 Commerce St, Glastonbury, CT 12 Dec 2025

Holiday Vendor Market 2025

The Glastonbury Boathouse 13 Dec 2025

Cookies and Photo with Santa

2450 Main Street, Glastonbury, CT, United States, Connecticut 06033 20 Dec 2025

Business After Hours

Glastonbury's Berkshire Hathaway HomeServices New England Properties 4 Dec 2025

CT Oral Health Initiative Holiday Celebration & Fundraiser

Crystal Ridge Winery 11 Dec 2025

PGA HOPE for the Holidays

Oakwood Virtual Golf 14 Dec 2025

Winter Whimsy Walk

The Shops at Somerset Square 6 Dec 2025

Family Bingo at Chick-fil-A Glastonbury

Chick-fil-A 1 Jan 2026

Holiday Cake Decorating Class with Ben & Jerry's Glastonbury

Ben & Jerry’s 14 Dec 2024