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March 2025

how to book wedding entertainment

The Ultimate Guide on How to Book Wedding Entertainment for Your Big Day

The Ultimate Guide on How to Book Wedding Entertainment for Your Big Day 2560 1709 adam Michaels

Congratulations!!! You’ve already completed the absolute hardest part of getting married! You found the person you wanted to spend the rest of your life with and, great news, they want to spend the rest of their life with you, too! We promise, it only gets easier from here – no matter what challenges lie ahead, you have a steadfast partner by your side, ready to get through it all with you. 

Here Comes the Planning

Speaking of the challenges that lie ahead, first up is… wedding planning! Isn’t it funny how the best day of your life is also the one that requires the most planning? There’s a reason it’s called “the wedding industry” – it’s literally an industry all on its own, feeding so many sectors of the economy and requiring so many decisions from you and your fiancé. If you’re already feeling some decision fatigue, or even overwhelmed, it’s ok! While we can’t help you sort out your color scheme or choose which flavor of cake you want (though if you want help with the taste-testing, please let us know); we can make figuring out the entertainment side a whole lot easier! 

Why Entertainment Matters

First and foremost, it’s important for us to acknowledge – no, emphasize that the entertainment you book absolutely has the ability to make or break the evening. A sub-par bite of salmon is quickly forgotten, but an unenthusiastic emcee? Songs that keep people in their seats or crowding the buffet table? (Though if it’s only because the food is divine, well, our compliments to the caterer!) We positively shudder to think of the most terrifying thought of all: an EMPTY DANCEFLOOR. It’s the flow of the evening, the music, the dancing, the mood and vibes that stay with people long after the night is over. 

How to Book Wedding Entertainment That Fits Your Day

So how do you make sure you book the right entertainment for your big day? We should start by saying that you’ve come to the right place and that everything we’re about to explain or suggest are all things that we at Around Town Entertainment are capable of providing for your big day – so don’t be shy about asking! 

Setting the Scene: Ceremony Music

Let’s begin in the very same place your big day will: your ceremony! Objectively the most important part of your day (kind of the whole reason the rest of the day even happens), it’s important to set the right ambience for this moment and the rest of the day. Have you ever been to a wedding where the guests all filter in and find their seats in silence? Uncomfortable, isn’t it? It feels like everyone is listening in on your conversations and no one is quite sure when to be fully quiet because the ceremony itself is about to begin. This is the pre-ceremony, and we believe in filling it with lovely, acoustic interpretations of music appropriate to the event, either from a guitarist, a pianist, strings trio, or, our personal favorite, a strings trio paired with a pianist! 

Keeping the Energy Up: Cocktail Hour

Now, let’s talk cocktail hour. Admittedly, this part of the event is typically a little less for you than it is for your guests since you’ll often be busy finishing up with the photographer and taking a moment for yourselves as the newlywed couple you are. This makes it even more crucial that the energy and atmosphere stay lively for your guests since you aren’t there. That’s where the cocktail trio comes in! A pianist, guitarist, and a bassist make for a flawlessly balanced ensemble to once again play ambient music, perfectly suited to the moment and the environment, facilitating an effortlessly energetic social experience for all your guests. 

The Reception: All Eyes (and Feet) on the Dancefloor

Then, of course, there’s the reception. Some folks will choose to hire a DJ for their reception and all we can say is… their loss. While a DJ can be great at getting people onto the dance floor later in the evening, only a live band can truly provide the perfect level of nuance throughout the evening, ensure that dinner has the perfect level of background music playing softly beneath it, or seamlessly extend your First Dance’s intro just a little bit longer as you make your way to the dancefloor. A live band can read the crowd like no one else; they can make a horn riff really pop, or let a vocalist take a classic and elevate it to a whole new level. And our bandleaders have years of experience, making them the perfect and most trustworthy choice to emcee your event. All that’s left to do is decide which of our award-winning bands you want to play your big day! 

When the Party Keeps Going: The After Party

Of course, the night doesn’t haaaave to end when your reception does – did anyone say “After Party”?! This is where a DJ really shines – they can sync with our live bands so that the final notes of the band transition straight into the first notes the DJ pumps onto the dancefloor. This can be the perfect move for crowds that aren’t ready to call it quits and want to keep the dance party going for another hour or two. 

Budgeting for Entertainment

As with any part of your wedding, there is, of course, cost to consider. When you’re weighing these decisions, we feel it’s important to remember to not only consider what you get with us, but take the time to compare it to what you’ll get from others. We think you’ll find that the quality we provide is outstanding, and our rates are unbeatable in our tier of service. Most importantly, while some parts of your wedding might be right for the “less is more” mindset (who doesn’t love a tastefully minimalist centerpiece that lets your guests see one another around the table), we know that when it comes to entertainment, more is just right.

unique wedding entertainment

10 Unique Wedding Entertainment Ideas to Wow Your Guests

10 Unique Wedding Entertainment Ideas to Wow Your Guests 2560 1709 adam Michaels

You’re Getting Married! Let’s Make It a Day to Remember with Unique Wedding Entertainment!

The big day is fast approaching and you know three things for sure: 

  1. You’ve found the person you want to spend the rest of your life with. 
  2. You want to make sure your wedding is the best day of your life so far. 
  3. You want to make your wedding unique and stand out in every way possible. 

In phenomenal news, you’ve already done the most unique thing of all, guaranteed to wow your guests, and make your day one no one will ever forget – you booked Around Town Entertainment and our award-winning live wedding bands to provide the most incredible soundtrack to your big day! 

Of course, as the tristate area’s premiere wedding bands, we also have plenty of fantastic ideas for ways you can personalize your reception, and unique touches that will really set your day apart. Here are ten of our favorites! 

It Really is An Everlasting Love: The Anniversary Dance 

This one is becoming a little more well-known, but it’s by no means common! The Anniversary Dance is simple, yet sweet and fun: it starts by inviting every married couple onto the dance floor and then does a bit of a reverse snowball! Our bandleader will start by asking everyone who’s been married for less than a year to please exit the dancefloor, then people married a year, 5 years, and onward until, at last there’s only one couple left on the dancefloor – the folks who’ve been married the longest! This can be a sweet and fun way to celebrate the long-lasting marriages of the people you hold dear, and who serve as an inspiration to you and your partner. 

You’re My Inspiration: A Different Kind of Parent Dance

In a slightly similar vein to the idea of the Anniversary Dance, sometimes it’s a really sweet and lovely touch to have a Parent’s First Dance. Obviously, it isn’t actually your parents’ first time dancing with one another, but imagine how sweet a surprise it could be to have the bandleader invite your parents to the dancefloor, then proceed to play the song your parents used as their First Dance song at their own wedding! To make the moment all the sweeter you can take the moment to say a few words about how your parents’ love inspired your own and thanking them for teaching you to love the way you do. 

You’re Still The One: A Song for Your Grandparents

This one is similar to our last idea, but a little more conditional since not everyone is lucky enough to have both their grandparents around to see them tie the knot. If you’re one of the lucky ones though, this idea is a must. Grandparents aren’t as likely to come out onto the dancefloor for the songs you and your friends love, but we promise they can still bust a move to songs they know – and what better song than their own First Dance? We promise there won’t be a dry eye in the house if you incorporate this unique idea into your big day! 

How Sweet It Is: Cake Cuttings Deserve Soundtracks, too!

Lots of wedding traditions have come and go over the years, but through it all, the cake cutting withstands the test of time. So why let such an iconic moment go on without all the bells and whistles available? Choosing a song to underscore this sweet moment helps keep the whole evening feeling like it’s something out of a movie and helps smooth over any moment that feels awkward as you navigate frosting, knives, plates, and presence of just one elbow too many in a tight space. 

No Such Thing as a Champagne Problem 

Though personally, we think Colbie Callait’s ‘Bubbly’ is a better fit for the moment you and your new spouse pour a champagne tower! While the champagne tower itself might not be a terribly new idea, playing a song to match the moment and adding to the cinematic feeling of the day is definitely a unique thought, and one sure to make this moment stand out even more for your guests! 

Ready, Set, Smile!

It’s a big night full of all your favorite people, and somehow, there never seems to be enough time to get photos with all of them. Enter the Photo Dash! Picture this: the bandleader announces that for the course of the next song, you and your spouse will be running from table to table to take a picture with everyone seated there so everyone had better finish chewing and be ready to jump into that photo with their biggest “Cheese”! Talk about making a fun game out of a task that could otherwise seem tedious

Unique Wedding Entertainment: Haaang on Sloopy! Sloopy, Hang On!

Not everyone is lucky enough to meet their spouse in college, but college remains one of the most common places someone will meet their spouse – which tends to mean a lot of guests are alumni of the same university! A great way to get a lot of people onto the dance floor and hyped up quickly? Play your college’s song! Whether it’s Ohio State’s ‘Hang On Sloopy’ by The McCoys or ‘In Heaven There Ain’t No Beer’ for our Iowa and Wyoming fans, a college song is a sure way to get the party pumping

Limbo Lower Now!

Yup, you read that right. An idea as unique as it is fun, especially for crowds who are feeling loose and lively, or for kid-friendly weddings, Chubby Checker’s ‘Limbo’ paired with actually playing the game is a fun choice your guests are sure to love! 

Shoes Off!

It’s the Newlywed Game! This one is a bit more of a classic, but this game remains forever unique because not only are you and your partner totally unique, so is the person or people you choose to ask the questions. (We recommend choosing your funniest friends to host this one!)

Give Mom Her Flowers

She gave her all, raising you to be the woman you are, so who better to dedicate your bouquet to? Usually we’d play an appropriate song for a bouquet toss, why not play an equally appropriate song while you dedicate your bouquet to the woman who made you who you are?

Water’s Edge Resort and Spa: A Coastal Getaway in Your Backyard

Water’s Edge Resort and Spa: A Coastal Getaway in Your Backyard 645 430 adam Michaels

It’s well-known that Around Town Entertainment is the cream of the crop when it comes to live entertainment on your big day – our award-winning musicians have been some of Connecticut’s favorites for years! Which is why we feel very qualified to tell you about one of our favorite Connecticut venues to play and celebrate our fabulous couples. 

Picture this: the salty breeze ruffling your hair, the rhythmic crash of waves keeping time with your heartbeat, and the golden glow of the sun setting over the Long Island Sound as you say, “I do.” Welcome to Water’s Edge Resort & Spa, where coastal charm meets classic New England elegance, making it the ultimate backdrop for a wedding that feels like a sun-kissed dream.

Nestled along the shoreline in Westbrook, Connecticut, Water’s Edge isn’t just a venue—it’s a seaside escape. The kind of place where you can sip champagne on a private beach, indulge in a spa day before slipping into your wedding attire, and dance the night away with the ocean as your witness. It’s romance, relaxation, and revelry all wrapped up in one breathtaking package.

 

A Ceremony with a View

Water’s Edge serves up some serious ceremony options, and they’re all stunning. Want to walk down the aisle with your toes in the sand? The beach ceremony site offers an intimate setting where the horizon stretches endlessly behind you. The soft sound of waves lapping at the shore and the scent of salt in the air create an atmosphere that is effortlessly romantic. Prefer a more traditional setup with ocean views? The Garden Terrace is a lush, manicured space with a stunning gazebo that gives off major fairytale vibes. Picture yourself surrounded by blooming florals, a gentle sea breeze keeping the moment cool and refreshing, and your guests seated beneath twinkling bistro lights. No matter which ceremony locale you choose, you’re guaranteed a wedding album filled with swoon-worthy shots.

 

Reception Spaces that Wow

When it’s time to party, the resort’s reception spaces are just as dazzling. The Grand Ballroom is an absolute showstopper with floor-to-ceiling windows, twinkling chandeliers, and enough space for all your friends, family, and an impromptu conga line. The soaring ceilings and elegant decor set the tone for an unforgettable evening, whether you’re envisioning a black-tie affair or a barefoot-on-the-dance-floor kind of night. 

For a more intimate affair, the Water’s Edge Ballroom offers a cozy yet elegant setting, where every detail feels warm and personal. And let’s not forget the outdoor options—oceanfront cocktail hour on the terrace? Yes, please. Imagine your guests sipping signature cocktails while watching the sun sink into the horizon, the sky painted in shades of pink and gold. The transition from a scenic outdoor soiree to a lively, joy-filled reception is seamless at Water’s Edge.

 

A Feast to Remember

Speaking of cocktails, let’s talk about the food—because Water’s Edge doesn’t just deliver on scenery, it delivers on flavor. The catering team specializes in fresh, locally sourced cuisine that brings a little bit of the shoreline to your plate. Think buttery lobster rolls, elegant seafood towers, and the kind of filet mignon that makes you consider asking for seconds (or thirds—we don’t judge). Their signature dishes are crafted with the finest ingredients, ensuring that every bite is as memorable as the moment itself. 

Your menu is fully customizable, giving you the opportunity to create a dining experience that reflects your taste. Maybe it’s an elevated plated dinner, or perhaps a more relaxed yet equally indulgent buffet-style spread. And of course, your wedding cake will be as delicious as it is beautiful, courtesy of their talented pastry team. Whether you’re dreaming of a classic tiered masterpiece or a trendy naked cake adorned with fresh blooms, they’ll make sure it’s both visually stunning and absolutely delectable.

 

Beyond the Big Day

Now, let’s talk about the perks—because this resort isn’t just about the big day, it’s about the full wedding experience. Out-of-town guests will love the on-site accommodations, from cozy guest rooms to luxurious suites with ocean views. Having everyone in one place makes the entire celebration feel like a destination wedding without the need for a passport. Guests can arrive early, unwind in style, and soak in the coastal beauty before the big event.

The spa is a dream for pre-wedding pampering, whether you’re looking for a relaxing massage or the perfect glow-up facial. Picture a serene morning with your bridal party, sipping mimosas in plush robes while enjoying rejuvenating treatments that melt away any last-minute wedding jitters. And for those making a full weekend out of it, Water’s Edge offers everything from beach bonfires to sunset cruises—because why limit the celebration to just one day? Kick off the festivities with a welcome party by the fire or a post-wedding brunch overlooking the water. It’s the kind of place that makes extending the wedding weekend an absolute must.

 

The Perfect Beginning

At the end of the night, as you steal a quiet moment on the beach, barefoot in the sand, the stars reflecting on the waves, you’ll know you chose the perfect place to start forever. Water’s Edge Resort & Spa isn’t just a venue—it’s a feeling. A feeling of warmth, of effortless elegance, of pure, unfiltered joy. And isn’t that exactly what a wedding should be?

Inquire about booking your wedding at Water’s Edge Resort and Spa by visiting their website and connecting with their team!

Windham Manor: Where Classic Charm Meets Modern Luxury

Windham Manor: Where Classic Charm Meets Modern Luxury 1290 860 adam Michaels

You already made a top-notch choice for your wedding by choosing Around Town Entertainment and our award-winning bands to provide the soundtrack for your evening – but now we come to an equally important question: Where are we providing all this atmosphere

Picture this: rolling green hills, fresh mountain air, and a stunning Victorian mansion that feels like it was plucked straight out of a fairy tale. Welcome to Windham Manor, a hidden gem nestled in the heart of the Catskill Mountains, where weddings transform into weekend-long celebrations, and nature meets pure elegance.  

 

The Estate: A Perfect Blend of Elegance and Comfort

Windham Manor isn’t just a venue—it’s a 45-acre retreat designed for couples who want more than just a single day of magic. The centerpiece is the 11,000-square-foot Victorian mansion, an effortlessly charming yet modern space that can accommodate up to 24 overnight guests – perfect for couples who want their families or bridal parties around for a full weekend of fun. With 12 beautifully appointed bedrooms, including a luxurious bridal suite and a groom’s suite designed for pre-wedding relaxation, it’s the perfect spot to settle in, soak up the excitement, and truly enjoy the wedding weekend experience.  

 

Ceremony Sites: Nature’s Embrace

Of course, a stunning setting is nothing without the perfect space to say “I do.” Windham Manor offers multiple ceremony locations, each one with its own unique charm. If you’ve always dreamed of an open-air ceremony, the lush, manicured lawn provides sweeping views of the Catskills as your natural backdrop. For something a little more enchanted, the wooded ceremony site feels like stepping into a storybook, with towering trees and soft sunlight filtering through the leaves. And then there’s the pond—a quiet, reflective space that brings a serene, romantic energy to the moment you exchange vows. No matter where you choose, nature is always the guest of honor, adding an effortless beauty to every photo. (And imagine one of our fabulous string trios in any of those spaces? Simply stunning in every way – the acoustics are perfection.)

 

The Barn: Rustic Sophistication at Its Best

When it’s time to celebrate, Windham Manor delivers in grand style. The barn—a true showstopper—takes rustic sophistication to a whole new level. This is no ordinary barn. With soaring ceilings, elegant lighting, and an open, airy design, it can accommodate up to 350 guests without ever feeling crowded. It’s the kind of space that adapts to any wedding style, whether you’re leaning into full-on rustic charm, modern elegance, or something in between. Picture candlelit tables, a packed dance floor, and the kind of atmosphere where laughter and happy tears blend together seamlessly.  

 

Amenities and Services: Thoughtfully Curated for a Seamless Experience

Windham Manor doesn’t just provide a venue—it creates an experience. From the moment you arrive, the dedicated on-site team ensures that every detail is seamless, from coordinating with top-tier vendors to helping you bring your unique vision to life. Catering partnerships with renowned chefs, like those from Mazzone Catering, guarantee that your guests will be talking about the food just as much as the stunning views. Whether it’s a curated cocktail hour, an interactive dinner station, or a gourmet dessert spread, the culinary options are as memorable as the setting itself.  

 

Beyond the Big Day: A True Lovers’ Retreat

Beyond the wedding day, Windham Manor offers a chance to slow down and savor the celebration. Guests can spend the weekend exploring the walking and hiking trails, enjoying nearby golf courses, or simply unwinding in the fresh mountain air. The nearby town of Windham is packed with charming restaurants, art galleries, and local attractions, making it easy to turn a wedding weekend into a full-blown getaway.  

 

Accolades and Testimonials: A Legacy of Excellence

It’s no surprise that Windham Manor has racked up glowing reviews from couples who’ve tied the knot here. One bride raved, “Windham Manor was hands down the most amazing wedding venue. I cannot rave about them enough! Susan and Barry were so professional, wonderful, and helpful throughout the process. They truly created a dream come true wedding venue and ended up being extended family by the end of the weekend.” That’s the kind of experience this venue delivers—not just a beautiful setting, but a warm, welcoming atmosphere that makes every guest feel like part of something special.  

For couples looking for a venue that goes beyond the ordinary, Windham Manor offers an absolutely perfect blend of luxury, nature, and heartfelt hospitality. It’s not just a place to get married—it’s a place to celebrate, to connect, and to create lifelong memories. If your wedding vision includes breathtaking views, a weekend of celebration, and a venue that truly understands how to make every moment magical, Windham Manor is ready to bring that vision to life. 

Tie the Knot at The Inn at Longshore: Where Coastal Charm Meets Timeless Elegance

Tie the Knot at The Inn at Longshore: Where Coastal Charm Meets Timeless Elegance 1600 727 adam Michaels

Dreaming of a wedding that feels like a scene straight out of a romantic movie? Coming right up! Around Town Entertainment and our award-winning musicians have the perfect soundtrack covered. But what about the “where”? Look no further than The Inn at Longshore in Westport, Connecticut! Nestled along the picturesque Long Island Sound, this venue offers a blend of New England charm and modern sophistication that’s sure to make your special day unforgettable.

 

A Waterfront Wonderland

Imagine exchanging vows with the gentle sound of waves as your soundtrack and a breathtaking sunset as your backdrop. At The Inn at Longshore, this dream becomes a reality. As the only waterfront event space in Westport, it provides stunning views that will leave you and your guests in awe. Whether you choose to say “I do” beneath a floral-adorned arbor on the lawn or inside the elegant ballroom, every moment will feel like a fairytale.

 

The lush greenery and serene coastal setting make this venue a perfect choice for couples who want a romantic outdoor ceremony. And if you’re worried about unpredictable weather, don’t be! The Inn at Longshore is well-equipped with indoor options that are just as breathtaking. Either way, the water views are a guarantee.

 

Versatility Meets Elegance

Whether you’re planning an intimate gathering or a grand celebration, The Inn at Longshore has you covered. The Grand Ballroom, adorned with large windows that let in an abundance of natural light, offers a spacious dance floor perfect for dancing the night away. The neutral tones and classic decor make it easy to customize, allowing you to bring your wedding vision to life.

 

For those who prefer an outdoor affair, the venue’s manicured lawns overlooking the water provide a serene setting for ceremonies and cocktail hours alike. Imagine sipping on signature cocktails while watching sailboats glide across the Sound—pure magic. And when the sun sets, the venue transforms into an intimate, candlelit paradise that exudes romance.

 

Culinary Delights

Let’s talk food—because what’s a wedding without a feast? The Inn at Longshore takes pride in its from-scratch culinary experience, featuring seasonal fare that will tantalize your taste buds. Their in-house catering team creates dishes that are as beautiful as they are delicious, with menus that can be customized to reflect your personal style and preferences.

 

From exquisite hors d’oeuvres to decadent plated dinners, the options are endless. Want a raw bar? Done. Dreaming of a late-night snack station with mini lobster rolls and gourmet sliders? Consider it handled. Whatever your vision, their culinary team is dedicated to delivering a dining experience that guests will rave about long after the last dance.

 

Accommodations with a Personal Touch

One of the perks of choosing The Inn at Longshore is the convenience of on-site accommodations. With 12 charming guest rooms, you and your closest loved ones can extend the celebration. No need to rush off at the end of the night—wake up to serene water views and enjoy a post-wedding brunch with your nearest and dearest.

 

Having accommodations right at the venue is a huge plus for out-of-town guests, making travel logistics a breeze. Plus, who wouldn’t want to spend the morning after their wedding sipping coffee while gazing out at the water?

 

Picture-Perfect Moments

With its stunning waterfront backdrop, historic architecture, and manicured gardens, The Inn at Longshore is a photographer’s dream. Whether you’re envisioning romantic golden-hour portraits, fun bridal party shots by the docks, or a grand exit under twinkling string lights, every corner of this venue is Insta-worthy.

 

Couples often take advantage of the venue’s beautiful surroundings for their first look, capturing those private, emotional moments before the ceremony. The sweeping staircases, lush greenery, and elegant indoor spaces offer endless opportunities for breathtaking photos that you’ll treasure forever.

 

Rave Reviews

Don’t just take our word for it. Couples have praised The Inn at Longshore for its exceptional service and unforgettable ambiance. One bride shared, “Our wedding at the Inn at Longshore was by far the best day of our lives. Everything was top notch—the venue is set on the Long Island Sound and feels like you are getting married in Cape Cod.” Another couple raved about the staff’s attention to detail, ensuring that every aspect of their day was flawless.

 

Who’s It Perfect For?

If you’re a couple who loves the idea of a coastal wedding but doesn’t want the hassle of a destination event, The Inn at Longshore is a dream come true. It’s perfect for:

Classic romantics who want an elegant yet inviting atmosphere

– Couples looking for a waterfront venue with both indoor and outdoor options

– Foodies who want a customized, elevated dining experience

– Anyone who wants a stress-free experience with on-site accommodations and expert staff

 

At The Inn at Longshore, your happily ever after begins with a picturesque setting, exceptional service, and memories that will last a lifetime.

Inquire about booking your wedding at The Inn at Longshore by visiting their website and connecting with their team!