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 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.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
You are going to want to save this…☀️ If you only have one day in Miami, base yourself in Downtown Miami.
You’re on the water, minutes from the cruise port, and about 10–15 minutes from some of the city’s most interesting neighborhoods. For a short stay, it makes logistics simple and food access… dangerously convenient.
Efficient. Walkable. Well-connected. If time is tight, this is how you make it count. 🌴✨
Yes. Sanguich is worth it. 🥪😍 It works because it doesn’t try to be trendy. No fusion twist. No reinvention. Just the classics done correctly.
Roasted pork done right.
Bread pressed properly.
Flavors that actually make sense together.
It feels nostalgic. Intentional. Rooted in culture. And it’s easily one of the best lunch stops in Downtown Miami. If you’re near Bayside Marketplace wondering where to eat this is a simple answer.✨
Thinking about the Waterfalls of Damajagua in Puerto Plata for your Virgin Voyages excursion?🌊 Important context: I am not a thrill girl. Roller coasters make me queasy. And I still loved this.
The 27 Waterfalls of Damajagua are like a 5/10 intensity. Adventurous but very doable. Guided. Safe. Not extreme.
You can choose your comfort level and that’s what makes it so good.😍
#damajagua #puertoplatacity #dominicanrepublic🇩🇴 #waterfalls #adventure
If you’re docking in Puerto Plata and don’t want to book an excursion, this is such an easy way to spend a few hours. You can walk straight from Taino Bay. It’s flat, manageable, and felt safe with a really good mix of colorful photo ops and actual city energy.
If you only have 1–2 hours, prioritize:
📍 Umbrella Street
📍 Pink Street
📍 Centro Histórico
Have more time? Add the Malecón de Puerto Plata. Into history? Stop by Fortaleza San Felipe. We were there during La Vega Carnival, which made everything feel extra lively, but even without a festival, I’d still recommend this route.
It’s simple. It’s realistic. And it gives you a look at Puerto Plata beyond just the cruise port. 🌴✨ Save this for your next stop.
#travelling #puertoplata #dominicanrepublic #downtownpuertoplata #travelitinerary
If you’re cruising into Taino Bay, here’s what you actually need to know. I was genuinely surprised. It’s clean, modern, and way more built out than I expected. Shops, photo spots, a lazy river, restaurants you could easily spend a few hours here without feeling bored.
I left for an excursion, but coming back and spending the afternoon inside the port was actually… nice. Easy. Low stress.
If you want adventure or deeper culture, leave the port. If you want a relaxed day? You truly don’t have to. Save this for your Puerto Plata stop & read the full blog now! 🌴
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