Boston is one of those cities that just feels alive when there’s an event happening — and there almost always is. Whether it’s tens of thousands of flags fluttering on Boston Common in May or confetti raining down during a North End feast in August, Boston knows how to celebrate.
Here’s my guide to the best Boston festivals and holidays — from patriotic moments that will give you goosebumps to foodie events you’ll be talking about for years.
If you’re in Boston for Memorial Day weekend, make your way to Boston Common. Every year, Home Base volunteers plant 37,000 flags on the Soldiers and Sailors Monument hill — one for each Massachusetts service member who has died in the line of duty since the Revolutionary War.
It’s quiet, powerful, and absolutely breathtaking. If you’re a photographer, go early morning or at golden hour to catch the soft light across the sea of flags.
Patriots’ Day (the third Monday in April) is uniquely Boston — it commemorates the battles of Lexington and Concord and doubles as Marathon Monday. The Boston Marathon is the world’s oldest annual marathon, and even if you’re not running, being part of the cheering crowd is an experience.
Head to Boylston Street near the finish line or plant yourself in Brookline or Newton to catch the runners tackling Heartbreak Hill.
Boston takes Independence Day seriously — and what better place to celebrate than one of the birthplaces of the Revolution?
Head to the Charles River Esplanade for the Boston Pops Fireworks Spectacular. It’s an all-day event with live music, picnics, and one of the best fireworks shows in the country.
Boston’s North End is already basically Italian Disneyland, but during St. Anthony’s Feast, it levels up. The last weekend of August, Hanover Street is closed to traffic and filled with food stalls, confetti parades, marching bands, and crowds of hungry locals and visitors.
This is New England’s largest Italian festival, and it’s been going strong for over 100 years.
What to eat:
Arancini (fried rice balls)
Italian sausages with peppers & onions
Zeppole (Italian fried dough)
And, of course, a stop at Mike’s or Modern Pastry for a cannoli
Pro tip: If you want a quieter North End experience, avoid this weekend — but if you want to be in the heart of the party, this is the time to go.
If you’re visiting during August, don’t miss my guide to St. Anthony’s Feast in Boston’s North End—it’s one of the city’s biggest annual celebrations.
The third weekend of October brings Head of the Charles, the largest two-day rowing event in the world. Even if you don’t know the first thing about crew, it’s a beautiful excuse to spend the day along the river, sipping cider and cheering as boats glide by with the fall foliage in the background.
Boston does cozy winter vibes really well. In December, Boston Common is lit up with a massive Christmas tree and holiday lights, and Faneuil Hall Marketplace hosts Blink! — a light and sound show. Add in ice skating on Frog Pond and hot chocolate from Tatte, and you’ve got a Hallmark-movie-level evening.
Boston knows how to throw a festival. Whether you’re standing in awe of 37,000 flags on Memorial Day, eating your way through St. Anthony’s Feast, or bundled up watching fireworks over the Charles, these holidays and events let you experience the city at its most alive.
Plan your trip around one of these celebrations, and you’ll leave with a camera roll full of photos, a stomach full of food, and maybe even a little confetti in your suitcase. For an up-to-date list of annual events, check out BostonUSA’s official event calendar. Planning your trip around the seasons? Read my Best Time to Visit Boston guide to see which festivals align with the best weather
Sedona got me again 🌵
This was my second trip, and somehow I liked it even more. Every visit adds another trail, viewpoint, or restaurant to the list, and the list keeps getting longer. This time I stayed near Airport Mesa, with sunsets right outside my door and none of the crowds.
My Substack has everything I’d tell a first-time visitor: the lodge I’ve now stayed at twice, the experiences I’d do first, and the restaurants I’d plan my days around.
Subscribe for free so you don’t miss the next one. Link in bio ✨
YES is always the answer... ✈️
I’m Wendy, and yes, I travel for a living (still pinching myself). After 15 years teaching middle school math, I traded the whiteboard for a passport and never looked back. Knoxville is home base, but Arizona sunsets are on another level, and if it’s been sitting on your list, this is your sign to finally say yes and book it. City guides, hotel reviews, and foodie spots are all on the blog. So glad you’re here 🌵☀️
A café, bakery, market, and wine shop all in one Phoenix stop 🍊
At La Grande Orange, order the crepes first, they’re the thing I’d go back for. The chicken salad sandwich is perfect if someone wants lunch while you’re still on breakfast, and the red velvet mini cupcake and a chai latte round it out. The sea salt chocolate chip cookie is heartier than gooey, so it’s best for dunkers. It’s counter service with easy parking, and the market has quirky gifts you won’t find elsewhere. Leave time to browse, because you’ll stay longer than planned.
Save this for your Phoenix trip ☀️
“Outside Terminal 3” is not a pickup location at PHX.
Before your driver pulls in, text them four things: your terminal, north or south side, door number, and inner or outer curb. Grab your bags first, then call them in. Drivers can wait free in the cell phone lot instead of circling. Getting through security is easy; getting picked up is the hard part.
Save this for your Phoenix trip ✈️
Come for the architecture, stay for the view.
The Chapel of the Holy Cross has been built into Sedona’s red rocks since 1956. The outside overlooks get busy, but inside is quiet, with huge windows framing the rocks. It’s free, takes 30-45 minutes, and has a paved, wheelchair-accessible ramp. Make sure to bring water in summer.
Save this for your trip planning!
Follow @travelwithwendyplummer for Beautiful Beach Destinations, City Guides, Foodie Spots, and Luxury Hotel Recommendations.
